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MX2008014108A - Benzimidazole modulators of vr1. - Google Patents

Benzimidazole modulators of vr1.

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Publication number
MX2008014108A
MX2008014108A MX2008014108A MX2008014108A MX2008014108A MX 2008014108 A MX2008014108 A MX 2008014108A MX 2008014108 A MX2008014108 A MX 2008014108A MX 2008014108 A MX2008014108 A MX 2008014108A MX 2008014108 A MX2008014108 A MX 2008014108A
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MX
Mexico
Prior art keywords
phenyl
benzimidazol
vinyl
benzenesulfonamide
trifluoromethyl
Prior art date
Application number
MX2008014108A
Other languages
Spanish (es)
Inventor
Wenxi Pan
William H Parsons
Jian Liu
Raul R Calvo
Mark R Player
Scott L Dax
Michael Brandt
Sharmila Patel
Wing S Cheung
Michele C Jetter
Yu-Kai Lee
Mark A Youngman
Kenneth M Wells
Derek A Beauchamp
Original Assignee
Janssen Pharmaceutica Nv
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Publication date
Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv
Publication of MX2008014108A publication Critical patent/MX2008014108A/en

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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A—HUMAN NECESSITIES
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
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    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Abstract

The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.

Description

BENCIMIDAZOLIC MODULATORS OF CAPSAICINE RECEIVER ÍVRD CROSS REFERENCE TO RELATED REQUESTS This present application claims the benefit of the United States Provisional Patent Application Act No. 60/797504, filed May 3, 2006, which is incorporated herein in its entirety as a reference and for all purposes.
BACKGROUND OF THE INVENTION Harmful chemical, thermal, and mechanical stimuli excite the peripheral nerve endings of small-diameter sensory neurons (nociceptors) that are derived from sensory ganglia (eg, dorsal root ganglia, nodes, and trigeminals) and initiate signals that are perceived as pain. Such nociceptive (i.e. nociceptor) neurons are critical for the detection of damaging or potentially harmful stimuli (eg, thermal, chemical and / or harmful mechanical) arising from changes in the extracellular environment during inflammatory, ischemic or otherwise traumatic and causing or have the potential to cause tissue damage (Wall, PD, and Melzack, R., Textbook of Pain, 1994, New York: Churchill Livingstone).
The nociceptors transduce harmful stimuli in depolarization of the membrane that produce an action potential, their subsequent conduction to the CNS and finally the perception of pain, discomfort, etc., as well as certain responses to it. At the molecular level, nociception is carried out by ion channels and / or receptors. It is known that vanilloid compounds derived from plants (eg, capsaicin and resiniferatoxin) selectively depolarize nociceptors and produce sensations of burning pain: the sensation that is typically caused by hot pepper chili peppers containing capsaicin. Consequently, capsaicin simulates the action of physiological / endogenous stimuli that activate the "nociceptive pathway". Recent advances in pain biology have identified a receptor, called VR1 (also known as capsaicin receptor or TRPV1) for vanilloids, protons and noxious heat. Because nociceptors are conductors of unwanted pain and inflammatory conditions in humans and animals, the modulation of their function is a valid strategy for palliative and other analgesic therapies. Compounds that are modulators (competitive and non-competitive agonists or antagonists [with respect to capsaicin and / or its recognition site] and allosteric modulators) of VR1 have a broad therapeutic potential, demonstrated by the clinical utility of commercially available pharmaceutical agents VR1, or the efficacy of VR1 modulators in animal models of diseases. Furthermore, it is recognized that the VR1 agonist modulators may possess a clinical utility that derives from their agonist properties, per se, and / or their ability to produce an agonist-mediated desensitization, which would indirectly manifest as a functional antagonism. Similarly, antagonist modulators could exhibit direct antagonistic (competitive or non-competitive) properties and / or indirect antagonism properties by means of the aforementioned desensitization mechanism. It is further recognized that positive and negative allosteric modulators can produce some or all of the functional consequences mentioned above and, as such, may also have clinical utility. Accordingly, this invention relates to each of these types of modulators. The effective use of VR1 agonists has been demonstrated in states of inflammatory, neuropathic and visceral pain. In an experimental human pain model, pretreatment with dermal capsaicin reduced the pain caused by the intradermal injection of an acidic solution (Bianco, ED¡ Geppetti, P. Zippi, P., Isolani, D., Magíni, B .; Cappugi, P. Brit J of Clin Pharmacol 1996, 41, 1-6), which suggests the benefit of VR1 agonists in the treatment of inflammatory pain. A particular role has been shown for VR1 agonists in inflammation and inflammatory pain: for example, resiniferatoxin prevented inflammatory hypersensitivity and induction of edema by carrageenan (Kissin, I.; Bright, C. A .; Bradley, E. L, Jr. Anesth Analg 2002, 94, 1253-1258). In addition, creams containing capsaicin (for example Axcain and Lidocare) are marketed for the relief of dermal pain related to diabetic neuropathy and post-herpetic neuralgia, indicating the usefulness of VR1 agonists for the treatment of neuropathic pain states . In addition, such creams have been shown to reduce postoperative neuropathic pain (Ellison, N., Loprinzi, CL, Kugler, J., Hatfield, AK, Miser, A., Sloan, J A., Wender, DB, Rowland, KM , Molina, R., Cascino, TL, Vukov, AM, Dhaliwal, HS and Ghosh, CJ Clin. Oncol. 15: 2974-2980, 1997). In cancer patients, it was shown that capsaicin contained in a caramel vehicle substantially reduces the pain of oral mucositis caused by chemotherapy and radiant therapy (Berger, A., Henderson, M., Naadoolman, W., Duffy, V Cooper, D., Saberski, L. and Bartoshuk, LJ Pain Sympt, Mgmt 10: 243-248, 1995. VR1 also plays a role in the physiology of bladder emptying, VR1 is expressed by the sensory neurons of The bladder, where it modulates the capacity to respond to fluid filling, The VR1 agonist resiniferatoxin desensitized the afferents of the bladder in a dose-dependent manner (Avelino, A., Cruz, F .; Coimbra, A. Eur. J Pharmacol 1999, 378, 17-22), which supports its use in the treatment of overactive bladder (Chancellor, MB, De Groat, WCJ Urol. (Baltimore) 1999, 162, 3-11). intravesicular of capsaicin or resiniferatoxin inhibited bladder contraction in both normal rats evils as in those injured in the spinal cord (Komiyama, I .; Igawa, Y .; Ishizuka, O .; Nishizawa, O .; Andersson, K.-E. J. Urol. (Baltimore) 1999, 161, 314-319), indicating the usefulness of VR1 agonists in incontinent patients with nerve injuries. The effectiveness of capsaicin or resiniferatoxin treatment in incontinence of patients with spinal cord injuries was confirmed in a clinical study (Seze, M .; Wiart, L; de Seze, M.-P .; Soyeur, L; Dosque, J.-P .; Blajezewski, S., Moore, N .; Brochet, B .; Mazaux, J.-M .; Barat, M .; Joseph, P.-A. Journal of Urology (Hagerstown, MD, United States) 2003, 171, 251-255). The effectiveness of VR1 agonists in reducing high blood pressure is suggested by the reduction with capsaicin in blood pressure of SHR and WKY rats (Li, J .; Kaminski, NE¡ Wang, DH Hypertension 2003, 41, 757 -762.). Capsaicin was also gastroprotective with respect to antral gastric ulcers (Yamamoto, H. Horie, S. Uchida, M., Tsuchiya, S., Murayama, T., Watanabe, K. Eur. J. Pharmacol., 2001, 432, 203-210). VR1 antagonists may also be useful in the treatment of inflammatory, neuropathic and visceral pain. For example, the therapeutic utility of VR1 antagonists has been demonstrated in visceral inflammatory conditions. VR1 is elevated in nerve fibers of the colon in patients with inflammatory bowel disease and VR1 antagonists alleviated pain and dysmotility (Yiangou, Y., Facer, P .; Dyer, NH; Chan, CL; Knowles, C; Williams, NS Anand, P. Lancet 2001, 357, 1338-1339). Intestinal inflammation induced by toxin A or dextran sodium sulfate in rodents was attenuated by VR1 antagonists (McVey, D.C. Schmid, P.C., Schmid, HHO, Vigna, SRJ Pharmacol. Exp. Ther. 2003, 304, 713-722). In addition, a synthetic antagonist of VR1 reduced the scores of colitis disease in several important endpoints, including macroscopic damage, microscopic epithelial damage, myeloperoxidase levels and diarrhea scores, which strongly supports the therapeutic use of antagonists. VR1 in inflammatory bowel diseases (Kimball, ES¡ Wallace, NH; Schneider, CR; D'Andrea, MR¡ Hornby, PJ Neurogasteroenterology 2004, 16, 811-818). The anatagonists of VR1 capsazepine and BCTC reversed mechanical hyperalgesia in models of inflammatory and neuropathic pain in guinea pigs (Walker, K. M.; Urban, L; Medhurst, S. J .; Patel, S .; Panesar, M. Fox, A. J .; Mclntyre, P. J. Pharmacol. Exp. Ther. 2003, 304, 56-62) and rats (Pomonis, J. D. Harrison, J. E. Mark, L. Bristol, D. R., Valenzano, K. J. Walker, K. J. Pharmacol. Exp. Ther. 2003, 306, 387-393). LPS-induced fever was attenuated in VR1-deficient mice (Lida, T., Shimizu, I, Nealen, L., Campbell, A., Caterina, M. Neurosci, Lett, 2005, 378, 28-33). . Increases in body temperature induced by VR1 agonists were suppressed by capsazepine, which indicates the utility of VR1 antagonists in the treatment of pyresis (Ohnluki, K. Haramizu, S., Watanabe, T., Yazawa, S .: Fushiki, TJ Nutr. Sci. Vitaminol. (Tokyo) 2001, 47, 295-298). VR1 agonists also modulate body temperature and fever. In the ferret, rat and mouse, the administration of resiniferatoxin induced hypothermia (Woods, A.J., Stock, M.J., Gupta, A.N., Wong, T.T.L., Andrews, P.L.R. Eur. J. Pharmacol., 1994, 264, 125-133). In addition, fever induced by phase I LPS (lipopolysaccharide) does not occur in desensitized animals with low intraperitoneal doses of capsaicin (Romanovsky, A. A. Frontiers in Bioscience 2004, 9, 494-504). The therapeutic potential of VR1 antagonists in inflammatory bronchial conditions is demonstrated by the finding that these antagonize the bronchoconstriction induced by capsaicin and acids (Nault, MA, Vincent, SG, Fisher, JTJ Physiol. 1999, 515, 567-578) . The related findings demonstrate that the VR1 antagonist capsazepine attenuates the cough induced by anandamide in guinea pigs (Jia, Y., McLeod, RL Wang, X., Parra, L. E .; Egan, RW; Hey, JA Brit. J. Pharmacol., 2002, 137, 831-836). The VR1 antagonist capsazepine was shown to significantly reduce anxiety type behaviors in rats using the elevated cross maze (Kasckow, JW, Mulchahey, JJ, Geracioti, TD Jr. Progress in Neuro-Psychopharmacol and Biological Psychiatry 2004, 28, 291 -295). Thus, VR1 antagonists may have utility in the treatment of anxiety, panic disorders, phobias or other non-adaptive responses to stress. U.S. Patent 6,299,796B1 discloses electroluminescent elements comprising units of the formula: Accordingly, there is a need for potent modulators of VR1 and, in particular, of novel benzimidazole compounds that exhibit potent binding affinity for the VR1 ion channel of humans and rats. There is also a need for new benzimidazole compounds that act as potent antagonists and / or functional agonists of the VR1 ion channel of humans and rats. Finally, there is a need for new benzimidazole compounds that bind with high affinity to VR1 and also act as potent functional antagonists of the VR1 ion channel of humans and rats.
BRIEF DESCRIPTION OF THE INVENTION The present invention relates to a compound of Formula (I): a form thereof where R- ?, R2, R3a, R3b, R4, P, q, r, L and A-, are as defined herein and their use as powerful modulators of VR1. The present invention also relates to a method for treating a disease mediated by the ion channel VR1 in a subject requiring thereof comprising the administration to the subject of an effective amount of a compound of Formula (I). The present invention is also directed to a process for preparing a compound of Formula (I) and salts thereof.
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to compounds of Formula (I): and a form thereof where: the dotted lines between positions 1, 2 and 3 of Formula (I) indicate the positions of a tautomeric double bond, where when a double bond is formed between positions 1 and 2, then R3b is present and where, when a double bond is formed between positions 2 and 3, then R3a is present; p is 1 or 2; q is 0 or; r is 0, 1, 2 or 3; L is C1.3 alkyl, C2-3 alkenyl, C2-3 alkynyl or cyclopropyl; Ai is selected from the group consisting of phenyl, biphenyl, naphthyl, pyridinyl, quinolinyl and indole; each Ri is selected from the group consisting of hydroxy, cyano, halogen, formyl, carboxy, alkyl, Ci-6 haloalkyl, Ci-6 alkoxy, Ci-6 haloalkoxy, Ci-6 alkylcarbonyl, Ci-6 alkoxycarbonyl, Ci-6 alkylthio , C 1-6 alkylsulfonyl, C 3-8 cycloalkyl, C 3-8 cycloalkyl C 1-4 alkyl, C 3-8 cycloalkyl C 1-4 alkoxy, C 3-8 cycloalkyl-oxygen, amino, (C 1-6 alkyl) i-2-amino, (C 3 cycloalkyl) -8) i-2amino, (C3-8alkyl-aminocarbonylcycloalkyl, (C1-6alkyl) i-2-aminocarbonyl, C1-6-alkylcarbonylamino, d6-alkoxycarbonylamino, aminocarbonylamino, (C6-alkyl) i-2-aminocarbonylamino, alkylsulfonylamino Ci-6, alkylsulfinylamino C1.6, aminosulfonyl, (alkyl 01-4) 1.2 aminosulfonyl, aminosulfonylamino and (Ci-6 alkyl) i.2 aminosulfonylamino, wherein the alkyl is optionally substituted with Ci-8 alkoxy, amino, (alkyl) alkylcarbonylamino C-6, alkoxycarbonylamino Ci-6, aminocarbonylamino, (alkyl Ci-6) i-2 aminocarbonylamino, alkylsulfonylamino C1-6, aminosulfonylamino, (alkyl Ci-6) i-2aminosulfo nilamino, hydroxy and phenyl, wherein the phenyl is optionally substituted with one, two or three substituents independently selected from the group consisting of halogen, cyano, nitro, Ci-6 alkyl, C6 alkoxy, Ci-6 alkylthio and Ci-alkylsulfonyl. 6 and wherein each case of alkyl and alkoxy is optionally perfluorinated; R 2 is selected from the group consisting of halogen, C- alkyl, C 1-4 alkoxy, C 1-4 alkylsulfonyl, nitro, amino, (C 1-4 alkyl) i-2 amino and cyano, wherein, each case of alkyl and alkoxy is optionally perfluorinated; each R3a and R3b is selected from the group consisting of hydrogen and optionally perfluorinated Ci-4 alkyl; and each R 4 is selected from the group consisting of halogen, nitro, cyano, carboxy, Ci-6 alkyl, d-6 alkoxy, Ci-6 haloalkyl, Ci-6 haloalkoxy, Ci-6 alkoxy Ci-6 alkyl, CiC alkylcarbonyl -6, alkylthio Ci-6l haloalkylthio d-6, alkylsulfonyl Ci-6, haloalkylsulfonyl Ci-6, cycloalkyl C3-8, cycloalkyl-C3-8-alkyl d-, cycloalkyl-C3-8-alkoxy cycloalkyl-oxy C3-8, amino, (Ci-6 alkyl) i-2 amino, (C3-8 cycloalkyl) 1-2 amino, (C3-8 cycloalkyl C3-8 alkyl) i-2 amino, aminocarbonyl, (C-6 alkyl) -2-aminocarbonyl, C 1-6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, aminocarbonylamino, (C 1-6 alkyl) i-2 aminocarbonylamino, alkylsulfonylamino Ci-6, haloalkylsulfonylamino Ci-6, alkylsulfinylamino d-6 , aminosulfonyl and (Ci-4 alkyl) i-2 aminosulfonyl, wherein each alkyl case is optionally substituted with one, two or three substituents independently selected from the group consisting of Ci-8 alkoxy, amino, (alkyl d-4) 1 -2-amino, alkylcarbonylamino Ci-6, alkoxycarbonylamino d-6, aminocarbonylamino, (Ci_6 alkyl) i-2 aminocarbonylamino, alkylsulfonylamino Ci-6l oxo and hydroxy, and where each case of alkyl and alkoxy is optionally perfluorinated. An example of the present invention includes a compound of Formula (I) or a form thereof, where q is 0. An example of the present invention includes a compound of Formula (I) or a form thereof, wherein Ai is selected from A group consisting of phenyl, biphenyl, naphthyl, quinolinyl and indole. An example of the present invention includes a compound of Formula (I) or a form thereof, wherein each R-? is selected from the group consisting of hydroxy, halogen, formyl, C-6 alkyl, Ci-6 haloalkyl, Ci-6 haloalkoxy, Ci-6 alkylcarbonyl, C 1-6 alkoxycarbonyl, C-6 alkylthio, C 1-6 alkylsulfonyl, amino, aminocarbonyl, alkylcarbonylamino d-6, alkoxycarbonylamino Ci-6, alkylsulfonylamino C-6, aminosulfonyl, (alkyl C ^) -! ^ aminosulfonyl and aminosulfonylamino, where alkyl is optionally substituted by amino, (Ci-4 alkyl) i-2 amino , aminosulfonylamino or hydroxy, and wherein the alkyl is optionally perfluorinated. An example of the present invention includes a compound of Formula (I) or a form thereof, wherein R 2 is selected from the group consisting of halogen and alkyl wherein the alkyl is optionally perfluorinated.
An example of the present invention includes a compound of Formula (I) or a form thereof, wherein each R3a and F < 3b are selected from the group consisting of hydrogen and C1-4alkyl. An example of the present invention includes a compound of Formula (I) or a form thereof, wherein each R 4 is selected from the group consisting of halogen, carboxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 haloalkyl, haloalkoxy C -6, alkylcarbonyl d-6, haloalkylthio C1-6, alkylsulfonyl d-6, haloalkylsulfonyl Ci-6, (C1-6 alkyl) i-2 amino, (C6 alkyl) i-2 aminocarbonyl, alkylcarbonylamino C ^, C 1-6 alkylsulfonylamino and haloalkylsulfonylamino Ci-6, wherein alkyl and alkoxy are optionally perfluorinated. An example of the present invention includes a compound of Formula (I) or a form thereof, wherein p is 1 or 2; q is 0; r is 0, 1, 2 or 3; L is C1-3 alkyl, C2-3 alkenyl, C2-3 alkynyl or cyclopropyl; A is selected from the group consisting of phenyl, biphenyl, naphthyl, quinolinyl and indole; each Ri is selected from the group consisting of hydroxy, halogen, formyl, C-6 alkyl, Ci-6 haloalkyl, C-6 haloalkoxy, C 1-6 alkylcarbonyl, Ci-6 alkoxycarbonyl, Ci_6 alkylthio, C-6 alkylsulfonyl, amino, aminocarbonyl, alkylcarbonylamino Ci-6, alkoxycarbonylamino Ci-6, alkylsulfonylamino C-6, aminosulfonyl, (alkyl Ci-4) - | .2 aminosulfonyl and aminosulfonylamino, where the alkyl is optionally substituted by amino, (alkyl 01.4) 1.2 amino, aminosulfonylamino or hydroxy, and wherein the alkyl is optionally perfluorinated; R2 is selected from the group consisting of halogen and alkyl C1-4, wherein the alkyl is optionally perfluorinated; each R3a and is selected from the group consisting of hydrogen and Ci-4 alkyl; and each R 4 is selected from the group consisting of halogen, carboxy, Ci_6 alkyl, Ci-6 alkoxy, Ci-6 haloalkyl, Ci-6 haloalkoxy, Ci-6 alkylcarbonyl, Ci-6 haloalkylthio, Ci-6 alkylsulfonyl, haloalkylsulfonyl Ci- 6, (Ci-6 alkyl) i-2 amino, (Ci-6 alkyl) i-2 and aminocarbonyl, alkylcarbonylamino Ci-6, alkylsulfonylamino Ci_6 haloalkylsulfonylamino Ci-6, wherein alkyl and alkoxy are optionally perfluorinated. The present invention also relates to the compounds of Formula o o Ib: lb where: R1 is independently hydroxyl; halogen, Ci-6 alkanyl; Fluorinated Ci-6 alkanyl; Ci-6 alkanoyloxy; Fluorinated Ci.6 alkanoyloxy; alkthylthio d-6; fluorinated C1-6 alkanoylthio; C-i-e-alkylsulfonyl; Fluorinated Ci-6 alkanylsulfonyl; C3-8 cycloalkanyl; C3-8 cycloalkanyl; C- alkanyl; C3-8 cycloalkynyloxy; C3-8 cycloalkanyl; C-alkanoyloxy; Not me; (alkanyl (cycloalkyl) C3-8) i-2amino; (C3-8 cycloalkanyl C4) -2amino; cyano; aminocarbonyl; (Ci_6 alkanyl) i-2 aminocarbonyl; C 1-6 alkynylcarbonylamino; alkanylcarbonylamino 0 ^ 6 fluorinated; alkanoyloxycarbonylamino Ci-6; C6-6 alkylaminocarbonylamino; Ci-6-alkylsulfonylamino; Fluorinated Ci-6-alkylsulfonylamino; aminosulfonyl; (Ci-8 alkanyl) i-2 aminosulfonyl; (Ci-8 alkanyl) i-2 aminosulfonyl fluorinated; wherein the alkanyl in any substituent of the Ri containing alkanyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of amino, (alkanyl ??? 8)? -2-aminoalkyl, alkanoylcarbonylamino ducylcarbonylamino d-6 fluorinated; alkanoyloxycarbonylamino Ci-6; C6-6 alkylaminocarbonylamino; alkylsulfonylamino Ci-β; fluorinated C-6 alkanylsulfonylamino; halogen, oxo, hydoxyl, fluorinated alkanyl and C- | 8 alkanoyloxy; p is 1 or 2; R2 is independently selected from the group consisting of halogen; Ci-4 alkanyl; Ci.4 fluorinated alkanyl; Ci ^ alkanoyloxy; C-i-4 alkanoyloxy fluorinated Ci-6 alkyloxy; C-M alkylsulfonyl; fluorinated Ci-4 alkanylsulfonyl; nitro; (Ci-4 alkanyl) i-2 amino; cyano; n is 0 or 1; R3 is independently selected from the group consisting of hydrogen, C1-4 alkanyl and fluorinated alkanyl; L is C2-3 alkyl, Ai is selected from the group consisting of phenyl and naphthyl; R 4 is independently halogen, Ci-6 alkanyl; Fluorinated Ci-6 alkanyl; Ci-6 alkanoyloxy; Fluorinated Ci-6 alkanoyloxy; Ci-6 alkanthio; fluorinated Ci-6 alkanoyldio, C 1-6 alkylsulfonyl; fluorinated C1-6 alkylsulfonyl; C3-8 cycloalkanyl; C3-8 cycloalkanyl; C 4 alkanyl, C 3-8 cycloalkanyloxy; C3-8 cycloalkanyl; Ci-4-aminoalkyloxy; (C alcan-amino alkanyl; (C3-8 cycloalkanyl) - | .2amino; (C3-8 cycloalkanylC1-4alkyl) i.2amino; cyano; aminocarbonyl; (C6.6 alkanyl) 2 aminocarbonyl; C0-6 alkanylcarbonylamino; alkanylcarbonylamino Fluorinated Ci-6, C0-6 alkanoyloxycarbonylamino, C0-6 alkylaminocarbonylamino, Ci.sub.6 alkylsulfonylamino, fluorinated Ci.sub.6 alkylsulfonylamino, aminosulfonyl, (Ci-e alkynyl) i-2 aminosulfonyl, (Ci-8 alkynyl) i-2 aminosulfonyl fluorinated; the alkanyl in any Ri substituent containing alkanyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, oxo, hydroxyl, fluorinated alkanyl and Ci-8 alkanoyloxy, phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, C 1 alkanyl, fluorinated C 1-4 alkanoyl, C-alkanoyloxy fluororadio, C 1-4 alkylsulfonyl, fluorinated C 1-4 alkylsulfonyl, nitro cyano, r is 0, 1 or 2, and enantiomers. , diastereomers, tautomers, solvates and salts acceptable for pharmaceutical use thereof. An example of the present invention includes compounds and enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof selected from the group consisting of: Comp. 5 Comp. 6 Comp. 7 Comp. 17 Comp. 18 Comp. 19 Comp. twenty Comp. 41 Comp. 42 Comp. 43 Comp.
Comp. 57 Comp. 58 Comp. 59 Comp. 60 Comp. 65 Comp. 66 Comp. 67 Comp. 68 Comp. 69 Comp. 70 Comp. 71 Comp. 72 Comp. 73 Comp. 74 Comp. 75 Comp. 76 Comp.81 Comp.82 Comp.83 Comp.84 Comp.89 Comp.90 Comp.91 Comp.92 Comp. 97 Comp. 98 Comp. 99 Comp. 100 Comp.105 Comp.106 Comp.107 Comp.108 Comp.113 Comp.114 Comp.115 Comp.116 Comp.117 Comp.118 Comp.119 Comp.120 Comp.121 Comp.122 Comp.123 Comp.124 Comp.129 Comp.130 Comp.131 Comp.132 Comp.137 Comp.138 Comp.139 Comp.140 Comp.145 Comp.146 Comp.147 Comp.148 Comp. 149 Comp. 150 Comp. 151 Comp. 152 Comp. 153 Comp. 154 Comp. 155 Comp. 156 Comp.161 Comp.162 Comp.163 Comp.164 Comp. 169 Comp. 170 Comp. 171 Comp. 172 Comp.177 Comp.178 Comp.179 Comp.180 Comp.185 Comp.186 Comp.187 Comp.188 Comp.193 Comp.194 Comp.195 Comp.196 Comp. 201 Comp. 202 Comp. 203 Comp. 204 Comp.209 Comp.210 Comp.211 Comp.212 Comp. 213 Comp. 214 Comp. 215 Comp. 216 Comp. 217 Comp. 218 Comp. 219 Comp. 220 Comp. 225 Comp. 226 Comp. 227 Comp. 228 Comp. 233 Comp. 234 Comp. 235 Comp. 236 Comp. 241 Comp. 242 Comp. 243 Comp. 244 Comp. 249 Comp. 250 Comp. 251 Comp. 252 Comp. 257 Comp. 258 Comp. 259 Comp. 260 Comp.265 Comp.266 Comp.267 Comp.268 Comp. 273 Comp. 274 Comp. 275 Comp. 276 Comp.281 Comp.282 Comp.283 Comp.284 Comp. 289 Comp. 290 Comp. 291 Comp. 292 Comp. 297 Comp. 298 Comp. 299 Comp. 300 Comp.305 Comp.306 Comp.307 Comp.308 Comp.314 Comp.315 Comp.316 Comp.317 Comp. 334 Comp. 335 Comp. 336 Comp. 337 Comp. 338 Comp. 339 Comp. 340 Comp. 341 Comp. 346 Comp. 347 Comp. 348 Comp. 349 Comp.363 Comp.364 Comp.365 Comp.366 Comp. 375 Comp. 376 Comp. 378 Comp. 379 Comp. 380 Comp. 383 Comp. 384 Comp. 385 Comp. 386 Comp. 387 Comp. 388 Comp. 389 Comp. 404 Comp. 405 Comp. 406 Comp. 407 Comp.412 Comp.413 Comp.414 Comp.415 Comp. 417 Comp. 418 Comp. 420 Comp. 421 Comp. 422 Comp. 423 Comp.428 Comp.429 Comp.430 Comp.431 Comp.436 Comp.437 Comp.438 Comp.439 Comp. 440 Comp. 441 Comp. 442 Comp. 443 Comp. 444 Comp. 445 Comp. 446 Comp. 447 Comp.460 Comp.461 Comp.462 Comp.463 Comp.468 Comp.469 Comp.470 Comp.471 Comp. 507 Comp. 508 As modulators of the VR1 vanilloid ion channel, the compounds of Formula (I) are useful for treating a disease mediated by the ion channel VR1 in a subject in which the disease is affected by the modulation of one or more vanilloid receptors. Accordingly, the present invention relates to a method of treating a disease mediated by the ion channel VR1 in a subject requiring it comprising administering to the subject an effective amount of a compound of Formula (I) or a salt or solvate of the same Forms of the compounds The term "form" means, with reference to the compounds of the present invention, that such may exist, without limitation, as a salt form, stereoisomeric, crystalline, polymorph, amorphous, solvate, hydrate, ester, prodrug or metabolite. The present invention encompasses all these forms of the compounds and mixtures thereof. The term "isolated form" means, in reference to the compounds of the present invention, that such may exist in an essentially pure state such as, without limitation, an enantiomer, a racemic mixture, a geometric isomer (such as a stereoisomer c / '). so trans), a mixture of geometric isomers and the like. The present invention encompasses all of these isolated forms and mixtures thereof. Certain compounds of Formula (I) may exist in various stereoisomeric or tautomeric forms and mixtures thereof. The invention encompasses all of these compounds and mixtures thereof. The compounds of the present invention may be present in the form of pharmaceutically acceptable salts. For use in medicaments, "pharmaceutically acceptable salts" of the compounds of this invention refer to non-toxic or basic / cationic acid / anionic salt forms. Suitable salts acceptable for pharmaceutical use of the compounds of this invention include the addition salts with acids which, for example, can be formed by mixing a solution of the compound according to the invention with a solution of an acid acceptable for pharmaceutical use such as hydrochloric acid, sulfuric acid, fumaric acid, maleic acid, succinic acid, acetic acid, benzoic acid, citric acid, tartaric acid, carbonic acid or phosphoric acid. In addition, when the compounds of the present invention carry an acidic residue, suitable pharmaceutically acceptable salts may include the alkali metal salts, eg, sodium or potassium salts; alkaline earth metal salts, eg. calcium or magnesium salts; and salts formed with suitable organic ligands, e.g. quaternary ammonium salts. Thus, representative pharmaceutically acceptable salts include the following: adipate, benzenesulfonate, benzoate, bicarbonate, bisulfate, bitartrate, borate, bromide, calcium, camsylate (or camphor sulfonate), carbonate, chloride, choline, clavulanate, citrate, dihydrochloride, disodium, edetate, fumarate, gluconate, glutamate, hydrabamine, hydrobromide, hydrochloride, iodide, isothionate, lactate, malate, maleate, mandelate, mesylate, nitrate, oleate, pamoate, palmitate, phosphate / diphosphate, salicylate, sodium, stearate, sulfate, succinate, tartrate, trometan, tosylate, trichloroacetate, trifluoroacetate and the like. An example of the present invention includes the compounds of Formula (I) and a salt form thereof where the salt is selected from the group consisting of disodium, hydrochloride and sodium. The invention includes the compounds of various isomers and mixtures thereof. The term "isomer" refers to compounds that have the same composition and molecular weight but differ in the physical and / or chemical properties. Such substances have the same number and class of atoms but differ in structure. The structural difference can be in the constitution (geometric isomers) or in the ability to rotate the plane of polarized light (stereoisomers). The term "optical isomer" means isomers of identical constitution that differ only in the spatial organization of their groups. Optical isomers rotate the plane of polarized light in different directions. The term "optical activity" means the extent to which the optical isomer rotates the plane of polarized light. The term "racemate" or "racemic mixture" means an equimolar mixture of two enantiomeric species, where each of the isolated species rotates the plane of polarized light in the opposite direction so that the mixture is devoid of optical activity. The term "enantiomer" means an isomer that has a non-superimposable mirror image. The term "diastereomer" means stereoisomers that are not enantiomers. The term "chiral" means a molecule that in a given configuration can not be superimposable with its mirror image. This is in contrast to the achiral molecules, which can be superimposed with their mirror images. The invention is considered to include the tautomeric forms of all compounds of Formula (I). Furthermore, for the chiral embodiments of the invention, it is considered that the invention includes pure enantiomers, racemic mixtures in addition to mixtures of enantiomers having 0.001% to 99.99% enantiomeric excess. In addition, some of the compounds represented by Formula (I) can be prodrugs, ie, drug derivatives that possess superior administration and therapeutic value capabilities compared to the active drug. Prodrugs are transformed into active drugs by enzymatic or chemical processes in vivo. The two versions of mirror images other than the chiral molecule are also known as levo (left turn), abbreviated L, or dextro (right turn), abbreviated D, which depends on how the polarized light rotates. The symbols "R" and "S" represent the configuration of the groups around the stereogenic carbon atom (s). An example of an enantiomer-enriched form isolated from a racemic mixture includes a dextrorotatory enantiomer, where the mixture is substantially free of the levorotatory isomer. In this context, substantially free of the levorotatory isomer, it may be in a range comprising less than 25% of the mixture, less than 10%, less than 5%, less than 2% or less than 1% of the mixture in accordance with the formula:% levorotatory = (levorotatory mass) / (dextrorotatory mass) + (levorotatory mass) x 100 Similarly, an example of an enantiomer-enriched form isolated from a racemic mixture includes a levorotatory enantiomer, where the mixture is substantially free of the dextrorotatory isomer. In this context, substantially free of the dextrorotatory isomer may be in a range comprising less than 25% of the mixture, less than 10%, less than 5%, less than 2% or less than 1% of the mixture in accordance with the formula: dextrorotatory% = (dextrorotatory mass) / (dextrorotatory mass) + (levorotatory mass) x 100"Geometric isomer" means isomers that differ in the orientation of the substituent atoms in relation to a carbon-double bond carbon, with a cycloalkyl ring or with a bridged bicyclic system. Substituent atoms (other than hydrogen) on either side of a carbon-carbon double bond can be in the E or Z configuration. In the? -configuration, the substituents are on opposite sides in relation to the carbon-carbon double bond. "Z" configuration, the substituents are oriented on the same side in relation to the carbon-carbon double bond The scope of the present invention is intended to include such isomers? " and Z". Substituent atoms (other than hydrogen) attached to the ring system may be in a cis or trans configuration. In the "cis" configuration, the substituents are on the same side in relation to the plane of the ring; in the "trans" configuration, the substituents are of opposite sides in relation to the plane of the ring. Compounds having a mixture of "cis" and "trans" species are designated "cis / trans". The scope of the present is intended to include all the "cis" and "trans" isomers. The isomeric descriptors ("R," "S," "E," and "Z") indicate the atomic configurations in relation to a nuclear molecule and are used as defined in the literature. In addition, the compounds of the present invention can have at least one crystalline, polymorph or amorphous form. The plurality of such forms is included in the scope of the invention. In addition, some of the compounds may form solvates with water (i.e., hydrates) or common organic solvents (e.g., organic esters such as ethanolate and the like). The plurality of such solvates is also within the scope of this invention.
Chemical nomenclature and definitions Link lines drawn in an annular system of a substituent variable indicate that the substituent may be attached to any of the substitutable ring atoms. As used herein, the following terms include the following meanings (additional definitions are provided where deemed necessary throughout the specification). The definitions herein may specify that a chemical term has an indicated formula. The particular formula provided is not intended to limit the scope of the invention, but is provided as an illustration of the term and is intended to include the plurality of variations that those skilled in the art expect to be included.
Definitions The term "C 1-6 alkyl" or "alkyl" means a linear or branched hydrocarbon alkyl radical, comprising from 1 to 6 carbon atoms. Non-limiting examples include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, tertiary butyl (also referred to as / -butyl or tert-butyl), 1-pentyl, 2-pentyl, 3- pentyl, 1-hexyl, 2-hexyl, 3-hexyl and the like. The term also includes alkyl groups in any combination thereof (eg, Ci-2, Ci-3, Ci-4 and the like). An alkyl radical may be attached to a nuclear molecule where allowed by the available valences. The terms "C2-3 alkenyl" and "C2-3 alkynyl" mean linear or branched carbon chains having 2 to 3 carbon atoms, wherein a C2-3 alkenyl chain has at least one double bond in the chain and one chain C2-3 alkynyl has at least one triple bond in the chain. The alkenyl and alkynyl radicals can be attached to a central molecule where allowed by the available valences. The term "C6-alkoxy" or "alkoxy" means a straight or branched chain alkyl or alkyldiyl hydrocarbon radical that binds to the group of the formula -O-C1-6alkyl, which comprises from 1 to 6 carbon atoms. Examples include methoxy, ethoxy, propoxy, isopropoxy, butoxy and the like. The term also includes alkoxy groups and any combination thereof (eg, Ci-2, C -3, C -4 and the like). An alkoxy radical can be attached to a nuclear molecule where allowed by the available valences. The term "cycloalkyl" refers to a saturated or partially unsaturated monocyclic, polycyclic or benzofused, hydrocarbon ring system composed of 3 to 14 carbon atoms. Except where specified, the term includes the ring system cycloalkyl C3.8, cycloalkyl 03-10, cycloalkyl C5-6, cycloalkyl C5-8, cycloalkyl C5-12, cycloalkyl Ce-io, cycloalkyl cycloalkyl C3.i or cycloalkyl C3_14 benzofused. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, cyclooctyl, 1H-indenyl, indanyl, adamantanyl, 9H-fluorenyl, 1.2.3.4-tetrahydro-naphthalenyl, acenaphthenyl, bicyclo [2.2.1] heptenyl and the like. The C3- [4] cycloalkyl radicals can be attached to a nuclear molecule and further substituted with any atom when allowed by the available valences. The term "benzofused" used as a prefix for an annular system means a radical formed by any radical of the radical ring system fused with a benzene ring. The benzofused radical can be bound to a nuclear molecule by means of any ring of the bicyclic system and further substituted at any atom where permitted by the available valences. The term "aryl" refers to monocyclic or bicyclic aromatic ring systems containing 6 to 12 carbon atoms in the ring. Examples include phenyl, biphenyl, naphthalene, azulenyl, anthracenyl and the like. The aryl radicals can be bound by a nuclear molecule and further substituted at any atom where allowed by the available valences. The term "aromatic" refers to a cycloalkyl hydrocarbon ring system having an unsaturated p-conjugated electron system. The term "hetero" used as a prefix for an annular system, refers to the replacement of at least one carbon atom of the ring with one or more heteroatoms independently selected from a nitrogen, oxygen or sulfur atom, where the nitrogen and sulfur atoms can exist in any allowed oxidation state. Examples include rings where 1, 2, 3 or 4 ring members are a nitrogen atom or 0, 1, 2 or 3 ring members are nitrogen atoms and 1 member is an oxygen or sulfur atom. When allowed by the available valences, up to two adjacent ring members may be heteroatoms; where one hetero atom is nitrogen and the other is a heteroatom selected from N, S or O. The term "heterocyclyl" refers to a monocyclic, polycyclic or benzofused non-aromatic (ie, saturated or partially unsaturated) ring system. Annular heteroatoms are selected from at least N, O, S, S (O) or S02, where the nitrogen and sulfur atoms can exist in an allowed oxidation state Examples include 2H-pyrrole, 2-pyrrolinyl, 3-pyrrolinyl, pyrrolidinyl, 2-imidazolinyl (also referred to as 4,5-dihydro-1 H-imidazolyl), imidazolidinyl, 2-pyrazolinyl, pyrazolidyl, oxazolidinyl, tetrazolinyl, tetrazolidinyl, piperidinyl, morpholinyl, 1,4-dithianyl, thiomorpholinyl, piperazinyl, azetidinyl, azepanyl, dihydro-pyranyl, tetrahydro-furanyl, tetrahydro-thienyl, tetrahydro-pyranyl, tetrahydro-pyridazinyl, hexahydro-1,4-diazepinyl, hexahydro-1,4-oxazepanyl, 1,3-dioxolanyl, 1. 4-dioxanil, 1 .3-b enzodioxolyl (also referred to as benzo [1,3] dioxolyl), 2,3-dihydro-1,4-benzodioxinyl (also referred to as 2,3-dihydro-benzo [1,4] dioxinyl) and the like. Heterocyclyl radicals can be attached to a nuclear molecule and further substituted at any atom where permitted by the available valences. The term "heteroaryl" means a radical of the monocyclic, polycyclic or benzofused aromatic ring system. The heteroatom ring members are selected from at least one N, O, S, S (O) or SO2, where the nitrogen and sulfur atoms can exist in any allowed oxidation state. Examples include furanyl, thienyl, pyrrolyl, pyrazolyl, H-imidazolyl, isothiazolyl, isoxazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, 1H-tetrazolyl, 2H-tetrazolyl, 1 H- [1 .2.3] triazolyl, 2H- [1 .2.3] triazolyl, 4H- [1.2.4] triazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, indolyl, azaindolyl, indazolyl, azaindazolyl, isoindolyl, benzofuranyl, benzothienyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzoisoxazolyl, benzothiadiazolyl, benzotriazolyl, purinyl, 4H-quinolizinyl, quinolinyl, isoquinolinyl, cinnolinyl, phthazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthyridinyl, pteridinyl and the like. Radicals can be attached to a nuclear molecule and also be substituted at any atom when allowed by available valences. The term "C 1-6 alkoxy-C-6 alkyl" means a radical of the formula: -alkyl C 1 -O-C 1-6 alkyl. The term "C 1-6 alkoxycarbonyl" means a radical of the formula: -C (0) -0-C 1-6 alkyl. Examples include alkoxycarbonyl Ci-4. The term "C6 alkoxycarbonylamino" means a radical of the formula: -NH-C (0) -O-Ci-6 alkyl. Examples include C1-4 alkylcarbonylamino. The term "(Ci-6 alkyl) i-2 amino" means a radical of the formula: -NH-Ci 6 alkyl or -N (C 1 alkyl- Examples include (Ci_4 alkyl) i-2 amino. "(Ci-6 alkyl) i-2 amino-Ci-6 alkyl" means a radical of the formula: -alkyl-Ci-6-NH-Ci-6 alkyl or -alkyl-Ci-6 N (Ci-6 alkyl) 2. The examples include (C 1-6 alkyl amino alkyl) The term "(Ci-6 alkyl) i-2 aminocarbonyl" means a radical of the formula: -C (0) -NH-alkyl d-6 or -C ( O) -N (alkyIC- | .6) 2- Examples include (alkyl) The term "(Ci.6 alkyl) i-2 aminocarbonylamino" means a radical of the formula: -NH-C (0) -NH -alkyl C -6 or -NH-C (O) -N (C 1-6 alkyl) 2 Examples include (alkyl aminocarbonylamino The term "(C 1-4 alkyl) - | .2-amino-sulfonyl means a radical of the formula: S02-NH-C1-4alkyl -S02-N (C1-4alkyl) 2. The term "C1-6alkylcarbonyl" means a radical of the formula: -C (0) -C6alkyl. Examples include alkylcarbonyl C - The term "alkylcarboni lamino Ci-6"means a radical of the formula: -NH-C (0) -alkyl Ci-6. Examples include alkylcarbonylamino The term "alkylsulfonyl Ci-β" means a radical of the formula: -S02-Ci-6 alkyl. Examples include C1-4 alkylsulfonyl. The term "alkylsulfinylamino Ci-6" means a radical of the formula: -NH-S (0) -C 1-6 alkyl. The term "C 1-6 alkylsulfonylamino" means a radical of the formula: -NH-S02-Ci-6 alkyl. The term "C 1-6 alkylthio" means a radical of the formula: -S-C 1-6 alkyl. Examples include C 4 alkylthio. The term "amino" means a radical of the formula: -NH2. The term "C 1-6 amino-alkyl" means a radical of the formula: C 1-6 alkyl-NH 2. The term "aminocarbonyl" means a radical of the formula: -C (O) -NH2. The term "aminocarbonylamino" means a radical of the formula: -NH-C (O) -NH2. The term "aminosulfonyl" means a radical of the formula: -S02-NH2.
The term "aminosulfonylamino" means a radical of the formula: The term "(Ci-6alkyl) 1,2-aminosulfonylamino" means a radical of the formula: -NH-SO 2 -NH-Ci-6alkyl -NH-SO 2 -N (Ci -6 alkyl) 2. Examples include (C 1-4 alkyl) i-2-aminosulfonylamino. The term "aminosulfonylamino-d-6 alkyl" means a radical of the formula: -alkyl-C1-6NH-S02-NH2. The term "(alkyl d-6) -i-2 aminosulfonylamino-C 1-6 alkyl" means a radical of the formula: -alkyl-Ci-6-NH-SO 2 -NH-alkyl d-6 or -alkyl-Ci- 6NH-SO N (Ci-6 alkyl) 2. The term "carboxy" means a radical of the formula: -C (O) OH. The term "C3-8 cycloalkyl-d-6 alkyl" means a radical of the formula: -alkyl C-i-6-C3-8 cycloalkyl. Examples include C3-8 cycloalkyl-C1-4 alkyl. The term "C3-8 cycloalkyl-alkoxy d-6" means a radical of the formula: -O-alkyl d-6-C3-8 cycloalkyl. Examples include C3-8 cycloalkyl-C- alkoxy. The term "C3-8 cycloalkyl-oxy" means a radical of the formula: -O-C3-8 cycloalkyl. The term "(C3-8 cycloalkyl) i-2amino" means a radical of the formula: -NH- (C3-8 cycloalkyl) or -N (C3-8 cycloalkyl) 2. The term "(C 3-8 cycloalkyl.alkyl Ci-4) 1.2amino" means a radical of the formula: -NH-C 1 -C 8 alkylcycloalkyl or -Nalkylalkyl.
C3-8 cycloalkyl) 2. The term "formyl" means a radical of the formula: -C (O) H. The term "oxo" means a radical of the formula: = 0. The term "halogen" or "halo" means the group chloro, bromo, fluoro or iodo. The term "haloalkyl Cis" means a radical of the formula: - C1-6alkyl (halo) n, where "n" represents the amount of available Ci-6 alkyl valencies, which may be substituted with one or more halogen atoms while they remain stable. Examples include difluoromethyl, trifluoromethyl, trifluoroethyl, chloromethyl, and the like. The term "haloalkoxy Ci-6" means a radical of the formula: -O-alkyl Ci-6 (halo) n, where "n" represents the amount of available valences of the Ci_6 alkoxy, which may be substituted with one or more atoms of halogen while they remain stable. Examples include difluoromethoxy, trifluoromethoxy, trifluoroethoxy, chloromethoxy and the like. The term "haloalkylsulfonyl? -? -?" Means a radical of the formula: -SO2-Ci-6alkyl (halo) n, where "n" represents the amount of available valencies of C- | 6 alkyl, which may be substituted with one or more halogen atoms while they remain stable. Examples include trifluoromethylsulfonyl and the like. The term "haloalkylsulfonylamino Ci-6" means a radical of the formula: -NH-S02-alkyl Ci-6 (halo) n, where "n" represents the amount of available valencies of Ci-6 alkyl, which may be substituted with one or more halogen atoms while they remain stable. Examples include trifluoromethylsulfonyl and the like. The term "C 1-6 haloalkylthio" means a radical of the formula: -S-Ci-6alkyl (halo) n, where "n" represents the amount of available valences of C 1-6 alkyl, which may be substituted with one or more halogen atoms while they remain stable. The examples include trifluoromethylsulfonyl and the like. The term "perfluorinated" means a radical that is substituted with fluorine atoms to the extent that it is allowed by the available valencies while remaining stable. The term "substituted" refers to a nuclear molecule in which one or more hydrogen atoms have been replaced with one or more residues of functional radicals. The number that is allowed by the available valences limits the number of substituents. Substitution is not limited to the nuclear molecule, but it can also be produced in a radical substituent, by means of which the substituent radical is converted into a linking group.
Therapeutic Use As modulators of the VR1 vanilloid ion channel, the compounds of Formula (I) are useful in methods of treating a disease mediated by the ion channel VR1 in a subject in which the disease is affected by the modulation of one or more vanilloid receptors. Accordingly, the present invention relates to a method of treating a disease mediated by the ion channel VR1 in a subject requiring it comprising administering to the subject an effective amount of the compound of Formula (I) or a salt or Solvate of it. The term "ion-mediated disease VR1" refers to chronic or acute pain due to a disease that causes inflammatory pain, burning pain or postoperative pain. An example of the use of a compound of Formula (I) or a salt or solvate thereof includes the use in the manufacture of a medicament for the treatment of a disease mediated by the ion channel VR1, where the disease mediated by the ion channel VR1 it is chronic or acute pain due to the disease that causes inflammatory pain, burning pain or postoperative pain. An example of the use of the compound of Formula (I) or a salt or solvate thereof includes use as a medicine to treat a disease mediated by the ion channel VR1, where the disease mediated by the ion channel VR1 is chronic or acute pain due to the disease that causes inflammatory pain, burning pain or postoperative pain. The term "prodrug" means a compound of Formula (I) or a form thereof that is converted in vivo into a functionally derived form that may contribute to therapeutic biological activity, wherein the converted form may be 1) a relatively active form, 2) a relatively inactive form, 3) a relatively less active form; or 4) any form that results directly or indirectly from such in vivo conversions. Prodrugs are useful when said compound may be too toxic to be administered systemically, poorly absorbed by the digestive system or degraded by the body before reaching its target. The methods of the invention for the selection and preparation of suitable prodrug derivatives are described, for example, in "Desiqn of Prodruqs". ed. H. Bundgaard, Elsevier, 1985. The term "metabolite" means a form of the compound of Formula (I) or a form thereof converted in vivo by metabolism or a metabolic process to a derivative of said compound. The term "subject" as used herein, refers to a patient, such as an animal, mammal or human being, who has been the object of treatment, observation or experiment and is at risk of (or susceptible to) develop a disease that has or will produce chronic or acute pain mediated by the ion channel VR1, where the pain caused by the disease is inflammatory pain, burning pain or postoperative pain. The term "effective amount" refers to that amount of a compound of Formula (I) or a form, pharmaceutical composition, medicament or treatment thereof that stimulates the biological or medicinal response (such as inhibition, prevention or improvement of chronic pain or acute mediated by the ion channel VR1) in a tissue system, animal or human, which is being examined by a researcher, veterinarian, doctor, doctor, or other clinician, which includes relief of the symptoms of inflammatory pain, burning pain or pain post-operative treated. The effective amount of a compound of Formula (I) or a form thereof is from about 0.001 mg / kg / day to about 300 mg / kg / day. The term "pharmaceutical composition" refers to a product that contains a compound of Formula (I) or a form thereof, such as a product that comprises the specified components in the specified amounts, in addition to any product that results directly or indirectly from such combinations of the components specified in the specified quantities. The term "medicament" or "medicine" refers to a product that contains a compound of Formula (I) or a form thereof. The present invention includes the use of such a medicament for treating chronic or acute pain mediated by the ion channel VR1. The term "acceptable for pharmaceutical use" refers to molecular entities and compositions that are of sufficient purity and quality to be used in the formulation of a pharmaceutical composition, medicine or medicament of the present invention. Because human (clinical and over the counter) use and veterinary use are also included within the scope of the present invention, a formulation acceptable for pharmaceutical use should include a pharmaceutical composition, medicine or medicament for both human and veterinary use. The term "treatment" refers without limitation to the inhibition, improvement, facilitation of eradication, inhibition of progression or promotion of chronic or acute pain stasis mediated by the VR1 ion channel. For oral administration, the pharmaceutical composition, medicine or medicament is preferably in the form of a tablet containing, eg, 0.01, 0.05, 0.1, 0.5, 1.0, 2.5, 5.0, 10.0, 15.0, 25.0, 50.0, 100, 150, 200, 250 and 500 milligrams of a compound of Formula (I) or a form thereof for adjusting the dosage of the treated patient. The optimal doses will vary according to the factors associated with the particular patient treated (eg, age, weight, diet and time of administration), the severity of the condition being treated, the particular compound used, the mode of administration and the potency of the the preparation. The use of daily or post-periodic dosing administration can be employed. A representative compound of Formula (I) or a form thereof includes a compound selected from the group consisting of: Comp. Name 1 (E) -1- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzyldazol-5-yl}. phenol) -etanone, 2 (£) -1- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl-1 H-benzimid 3 (E) -2- { 2- [2 - (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.] -phenol, 4 (£) -N- (2-. {2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -acetamide, 5 (£) -2-. {2- 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -benzamide, 6 (£) -3- { 2- [2- (4-tert-butyl phenyl) -vinyl] -1H-benzyldazole-5-yl.} - benzamide, 7 (£) -4- { 2- [2- (4-tert-butyl-phenyl) -v Nyl] -1H-benzimidazol-5-yl.} -benzamide, 8 (£) -N- (4- { 2- [2- (4-ter-butyl- phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -acetamide, 9 (£) -N- (2- { 2- [2- (4-tert-butyl-phen l) -vinyl] -1 H-benzimidazole-5-yl.] - phenyl] -methanesulfonamide, ter-butyl ester of the acid (£) - (2-. {2- 2- [ 2- (4-tert-butyl-phenyl) -v] nyl] -1H-benzimidazol-5-yl} -phenyl] -carbamic acid, 11 (E) -2- { 2 - [2- (4-tert-butyl-pheny] -v '^ 12 (£) - (2- { 2- [2- (4-tert-butyl-pheny) -v L] -1 H-benzimidazol-5-yl.} - phenyl) -methanol, 13 (E) -2-. { 2- [2- (4-trifluoromethyl-enyl) -v] n-1] -1 H -benzimidazol-5-yl} -benzamida, 14 (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl} -phenoL 15 () -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl. ethanone, 16 (£) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl] -v] n-1] -1 H-benzimidazole-5-yl. .phenyl) -ethanol, 17 (E) -N- (2-. {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5 -l.}.-Phenyl] -methanesulfonamide, 18 (fE) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5- il.}.-phenyl) -propan-2-ol, 19 (£) -2- { 2- [2- (4-trifluoromethoxy-pheny] -vinyl] -1 H-benzimidazole-5 -l.} - benzamide, 20 (-r) -1- (2- { 2- [2- (4-trifluoromethoxy-phenol) -v] nyl] -1 H-benz Midazol-5-yl.} - phenyl) - ethanone, 21 (£) -1- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimido-20l-5-yl.}.-phenyl) -ethanol, 22 (E) -N- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl) -1 H- benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 23 (E) -2- (2- { 2- [2- (4-trifluoromethoxy-pheny) -v-n-1 ] -1 H-benzimidazol-5-yl.] -phenyl] -propan-2-ol, 24 (E) -N- (2- { 2- [2- (3.4-d Fluoro-fen L) -vinyl] -1H-benzimidazol-5-yl.] -phenyl] -acetamide, (N) (3-). { 2- [2- (3,4-difluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} phenyl) -acetamide, 26 (E) -2-. { 2- [2- (3,4-d.fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzamida, 27 (£) -1- (2- { 2- [2- (3,4-d.fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 28 ( £) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. { 2- [3- (4-tert-butyl-phenyl] -propyl] -1H-benzimidazol-5-yl} -phenol, 2- [3- (4-tert-butyl-phenyl) -propyl] -5-m-tolyl-1H-benzimidazole, Comp. Name 31 N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. { 2- [2- (4-tert-butyl-pheny] -ethyl] -1 H -benzimidazol-5-yl} -phenol, 33 3-. { 2- [2- (4-tert-butyl-phenyl] -ethyl] -1 H -benzyldazole-5-yl} -phenol, 34 4-. { 2- [2- (4-tert-butyl-phenyl) -etl] -1 H -benzyldazole-5-yl} -phenol, 35 (E) - (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenol) -metanol, 36 (E) -2-. { 2- [2- (4-Trifluoromethylsulfanyl-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} -phenol, 37 (£) -N- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -v-n-1] -1H-benzimidazole-5-yl. phenyl) -acetamide, 38 (E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, 39 (£) -1- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl} phenyl) -ethanone, 40 (E) -1- (2-. {2- 2- (4-trifluoromethanesulfonyl-phenyl) -v] nyl] -1H-benzyl Dazol-5-yl.} - phenyl) -ethanone, 41 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenol) -vinyl] -1H-benzimidazole-5-yl} - phenol, 42 (E) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl.} - phenol) -methanol, 43 (E) -N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenol) -v] nyl] -1H-benzyl Dazol-5-yl.} - phenyl) -acetamide, 44 (£) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -v] n-1] -1 H -benzyznidazol-5-yl} benzamide, 45 (E) -1- (2- { 2- [2- (4-trifluoromethanesulfoyl-phenyl] -vinyl] -1H-benzimidazole-5-yl. phenyl) -ethanol, 1- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanol, 47 ( E) -2- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenol) -v] nyl] -1 H -benzyldazol-5-yl.} - phenyl ) -propan-2-ol, 48 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl] -v] nyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl} - phenol, 49 (E) -3-. { 2- [2- (4-tert-butyl-pheny] -vinyl] -6-trifluoromethyl-1 H-benzimidazole-5-yl} - phenol, 50 (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benz Midazole-5-yl] -phenyl) -acetamide, 51 (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl.} - phenyl) -methanol, 52 (E) -2- [2- (4-tert-butyl-phenyl) -vinyl] -5- (2-fluoro-phenyl) l) -6-trifluoromethyl-1H-benzimidazole, 53 (£) -2-. { 2- [2- (4-tert-Butyl-phenyl] -vinyl] -6-trifluoromethyl-1 H-benzyldazol-5-yl} benzamide, 54 (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzimidazole-5 -yl.}. - phen.l) -carbamic acid tert-butyl ester, 55 (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -v. l] -6-trifluoromethyl-1H-benzyldazol-5-yl}. phenyl) -methanesulfonamide, 56 (£) -N- (2-. {6-trifluoromethyl-2 - [2- (4-trifluoromethy1-pheny1) -vinyl] -1H-benzimidazol-5-yl] -phenyl) -acetamide, Comp. Name 57 (E) -1- (2-. {6-Trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}-phenyl] -ethanone, 58 (.r) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzylnidazole- 5 - l.}. - phenyl) -methanol, 59 (и) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - phenol, 60 (£) -3-. { 6-fluoro-2-l2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenol, 61 (E) - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1H-benzamidazole-5 -yl.}. - phenyl) -methanol, 62 (£) -1- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenol) -v] nyl] -1 H -benzamidazol-5-yl.} - phenyl) -ethanone, 63 () -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenol) -vinyl] -1H-benzyldazole-5-yl} - benzamide, 64 (E) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-pheny] -vinyl] -1H-benzimidazol-5-yl .}. - phenyl) -acetamide, 65 (£) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1 H -benzinidazole -5-yl.} - phen.l) -methanesulfonamide, 66 (E) - (2-. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole-5-yl.} - phenyl) -methanol, 67 (£) -1- (2-. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v¡n¡ l] -1 H-benzyldazol-5-yl.} - phenol) -ethanone, 68 (£) -2-. { 6-Chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenol, 69 (£) -2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 70 (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H-benzimidazole-5-yl} - benzenesulfonamide, 71 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vin] -1-H-benzimidazol-5-yl} - benzenesulfonamide, 72 (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazole-5-yl); l.}.-phenyl] -methanesulfonamide, 73 (E) -C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethyl-phenyl) - vinyl] -1 H- benzyldazol-5-yl.] - phenyl] -methanesulfonamide, 74 (£) -C, C, C-trifluoro-N- (2- {.2 2- [2- (4-trifluoromethanesulfonyl-phenyl] -v] nyl] -1H-benzimidazol-5-yl}. Phenyl) -methanesulfonamide, 75 (£) -1- ( 2- {2- [2- (4-chloro-phenyl) -v] n-1] -1 H-benzimidazol-5-yl} -phenyl} -ethanone, 76 (E) -1- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.] -phenyl] -ethanol, 77 (E) -N- (2- { 2- [2- (4-chloro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 78 (£) -2- (2-. {2- 2- [2- (4-chloro-phenyl] -v] nyl] -1 H-benzimidazole-5-yl] -phenyl) -propan-2- ol, 79 (£) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, 80 ()) -N- (2- { 2- [2- (4-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -C, C, C- trifluoro-methanesulfonamide, 81 (£) -1- (2- {2- [2- (4-methanesulfonyl-phenyl) -vin] -1 H-benzimidazole-5-yl} - phenyl) - ethanone, 82 (iE) -1- (2- { 2- [2- (4-methanesulfonyl-pheny] -vinyl] -1 H -benzyldazol-5-yl.} - phenol) -ethanol, Comp. Name 83 (E) -N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 84 (£ ) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzyldazol-5-yl.} - phenyl] -propan-2-ol , 85 (£) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzyldazol-5-yl} - Benzenesulfonamide, 86 (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimddazol-5 -yl.}.-phenyl) -methanesulfonamide, 87 (£) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phen L] -v, n. 1. -1 H-benzimidazol-5-yl) -phenyl] -ethanone, 88 (£) -1- [2- (2-. {2 - (4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 89 (E ) -N- [2- (2- { 2- [4- (2,2,2-Trifluoro-1 -trifluoromethyl-ethoxy) -phenyl] -v] nyl.} -1 H- benz Midazole-5-yl) -phenyl] -metanesulfonamide, 90 (£) -2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-tr! fluoromethy1-ethoxy) -phenyl] -v1n1l. -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 91 (£) -2- (2-. { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -benzenesulfonam Da, 92 (£) -C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -v¡n¡l.} -1 H-benzimidazol-5-yl) -phenyl] -metanesulfonamide, 93 (E) -1- [2- (2-. {2- 2- [4 - (2,2,2-tnfluoro-ethoxy) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl) -pheny] -ethanone, 94 (£) -1- [2- (2-. { 2- [4- (2.2.2-trifluoro-ethoxy) -phenyl] -vinyl} -1H-benzamdazol-5-yl) -phenyl) -ethanol, 95 (£) -N- [2- (2-. {2- 2- [4- (2.2.2-trifluoro- ethoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 96 (£) -2-t2- (2-. {2 - [4- (2,2,2-trifluoro-ethoxy) -phenyl] -v, n-1., -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 97 (£) -2- (2- { 2- [4- (2,2,2-Trifluoro-ethoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 98 ( £) -C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -v-nil} -1 H- benzimidazole-5-yl) -phenyl] -methanesulfonamide, 99 (£) -1- [2- (2- { 2- [4- (2.2.3.3.3- pentafluoro-propoxy) -phenyl] -vinyl] -1 H-benzamidazol-5-yl) -phenyl] -ethanone, 100 (£) -1- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -v-n-1} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 101 (E) -N- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl. ) -phenyl] -methanesulfonamide, 102 (E) -2- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -vil .}. -1 H- benzimidazo l-5-yl) -phenyl] -propan-2-ol, 103 (£) -2- (2-. { 2- [4- (2.2.3.3.3-pentafluoro-propoxy!) -phenyl] -v¡n¡l} -1 H- benzimidazol-5-yl) -benzenesulfonamide, 104 (£) -C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2.2.3.3, 3-pentafluoro-propoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 105 (£) -1- (2- { 2 - [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl.] -phenyl] -ethanone, 106 (E) -1- (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethan 107 ( £) -N- (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl] -methanesulfonamide, Comp . Name 108 (£) -2- (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol , 109 (£) -2-. { 2- [2- (3-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 110 (£) -N- (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -C, C, C- trifluoro-methanesulfonamide, 111 (£) -1- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanone, 112 (E) -1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 113 (E) -N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 114 (£) -2- ( 2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 115 (E) -2-. { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 116 (£) -C, C, C-tnfluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} .-phenyl) -metanesulfonamide, 117 (£) -N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) - methanesulfonamide, 118 (E) -N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -vinyl) - phenyl] -methanesulfonamide, 119 (£) -N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide , 120 (£) -N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -vinyl ) - phenyl-methanesulfonamide, 121 (E) -2-. { 2- [2- (4-methanesulfonyllamine-phenyl) -v-n-1] -1H-benzyldazole-5-yl} - benzenesulfonamide, 122 (?) - 0.0.0-1 p ???? G? -? - (2- { 2- [2- (4-? t? 6? 3? 5 ???? ??? 3 ?? '??? -? T?' ??) - ????] - 1? - benzimidazol-5-yl.}.-Phenyl) -methanesulfonamide, 123 (£) -N- ( 4- { 2- [5- (2-Acetyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) -C, C, C-trifluoromethanesulfonamide, 124 (£) -C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl] -vinyl) phenyl] -methanesulfonamide, 125 (£) -C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1H-benzimidazol-2-yl] - vinyl.}. phenyl) -methanesulfonamide, 126 (£) -C, C, C-trifluoro-N- [4- (2- { 5- [2- (1-hydroxyl-1-met 1-ethyl) -phenyl] -1H-benzamidazol-2-yl] - vinynyl) -phenyl] -methanesulfonamide, 127 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyllamino-pheny] -vinyl] -1H-benzimidazole-5-l} -benzenesulfonamide, 128 (E) -C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-trifluoromethanesulfonyl-phenylamino) -1 H- benzimidazol-2-yl] -vinyl.}. phenyl) -methanesulfonamide, 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 130 2-. { 2- [2- (4-Trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 131 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 132 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenol) -ethyl] -1 H -benzimidazole-5-yl}. -phenyl] -metanesulfonamide, Comp. Name 133 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, 134 C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -etl] -1 H - benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 135 1- (2- { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H-benzyl dazol-5-yl.}.-phenyl) -ethanone, 136 1- (2- { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H -benzyldazole-5-yl .}.-phenyl) -ethanol, 137 N- (2- {2- [2- (4-chloro-phenyl) -ethyl} -1 H -benzimidazol-5-yl}. phen.l) -methanesulfonamide, 138 2- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 139 2-. { 2- [2- (4-chloro-phenyl) -etl] -1 H -benzyldazol-5-yl} -benzenesulfonamida, 140 N- (2- { 2- [2- (4-chloro-phenyl) -etl] -1 H -benzimidazol-5-yl.} - phenyl] -C, C , C-trifluoromethanesulfonamide, 141 1- (2-. {2- 2- (4-methanesulfonyl-phenol) -etl] -1 H-benzyl-2-azole; l.} .phenyl) -ethanone, 142 1- (2- { 2- [2- (4-methanesulfonyl-pheny] -etl] -1 H -benzyldazole-5- il.}.-phenyl) -ethanol, 143 N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -etl] -1 H -benzimidazol-5-yl.} - phenyl] -methanesulfonamide , 144 2- (2- { 2- [2- (4-methanesulfonyl-phenyl] -ethyl] -1 H -benzyldazole-5-yl.} - phenyl] - propan-2-ol, 145 2-. { 2- [2- (4-methanesulfonyl-pheny] -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 146 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -etl} -1 H -benzimidazole-5) 1.}. phenyl) -methanesulfonamide, 1-7- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -etl} -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 148 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-tr! fluoromethyl-ethoxy!) -phenyl] -ethyl.} -1 H -benzyldazol-5-yl) -phenyl] -ethanol, 149 N- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -etyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 150 2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -etyl} -1 H-benzyl midazol-5-yl) -phenyl] -propan-2-ol, 151 2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl) ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -benzenesulfonamide, 152 0.0.0-1 p ???? G? -? - [2- (2- { 2- [4- (2.2.2-1p ???? G? -1 -? G ????? G ?? t? ß ?? - ß ????) -? T ?? ?] - ethyl.} -1 H-benzyldazoI-5-yl) -phenyl] -methanesulfonamide, 153 1- [2- (2- { 2- [4- (2,2,2-tr Flupro-ethoxy) -phenl] -et l} -1 H-benc¡m¡dazol-5-¡l) -phenyl] -.. ethanone, 154 1- [2- (2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 155 N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -etl.} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 156 2- [2- (2- { 2- [4- (2,2,2-trifluoro- ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. {2- 2- [4- ( 2,2,2-trifluoro-ethoxy) -phenyl] -etyl] -1 H-benzimidazol-5-yl) -benzenesulfonamide, 158 C, C, C-trifluoro-N- [2- (2- {.2- [4- (2.2.2-trifluoro-ethoxy) -phenyl] -etyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 159 1 - [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -etanone, Comp. Name 160 1 - [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] Ethanol, 161 N- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) - phenyl] -methanesulfonamide, 162 2- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazole- -l) -phenyl] -propan-2-ol, 163 2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -pheny] -eti .} -1 H-benzyldazole-5-l) -benzenesulfonamide, 164 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2.2.3.3 , 3-pentafluoro-propoxy) -phenyl] -ethyl.} - 1 H-benzimidazol-5-yl) -phenyl] -metanesulfonamide, 165 1 - (2- { 2- [2- (3- chloro-phenyl) -ethyl] -1 H-benzimidazol-5-yl.}. -phenyl) -ethanone, 166 1- (2- {2- (2- (3-chloro-phenyl) -ethyl) ] -1 H-benzyldazol-5-yl.} - phenyl) -ethanol, 167 N- (2-. {2- 2- [2- (3-chloro-phenyl) -ethyl] -1 H-benzimidazol-5-yl.] - phenyl] -methanesulfonamide, 168 2- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H-benzimidazole-5 -yl.}. -f-enyl) -propan-2-ol, 169 2-. { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 170 N- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -C, C, C-trifluoromethanesulfonamide, 171 1 - (2- { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 172 1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 173 N- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl] -H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 2- (2-. 2- [2- (3-tnfluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 175 2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 176 C> C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 177 N- (4-. {2- 2- [5- (2-Acetyl-phenyl) -1 H -benzimidazol-2-yl) -ethyl} phenyl) -methanesulfonamide, 178 N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -ethyl) -phenyl ] - methanesulfonamide, 179 N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 180 N- [4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -ethyl) -phenyl] - methanesulfonamide, 181 2-. { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 182 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -metanesulfonamide, 183 N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -ethyl} -phenyl) -C, C, C-trifluoro methanesulfonamide, 184 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. - ethyl) -phenyl] -methanesulfonamide, 185 C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] -ethyl .}.-phenyl) -methanesulfonamide, 186 C, C, C-trifluoro-N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H-benzimidazol-2-yl.} - ethyl) -phenyl] -methanesulfonamide, Comp. Name 187 2-. { 2- [2- (4-trifluoromethanesulfonyllamine-phenol) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 188 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethanesulfonyl-phenyl) -etl] -1 H -benzimidazole-5 - l.}. - phenyl] - methanesulfonamide, 189 2-. { 2- [2- (4-Trifluoromethoxy-phenyl] -cyclopropyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 190 2-. { 2- [2- (4-trifluoromethyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl} - Benzenesulfonamide, 191 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 192 C, ClC-tr'ifluoro-N- (2- {2- [2- (4-tr'ifluoromethoxy-phenyl) -cyclopropyl] -1 H- benz Midazol-5-yl.}. Phenyl) -methanesulfonamide, 193 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] - 1 H- benzamidazol-5-yl.] - phenyl) -methanesulfonamide, 194 C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfon 1-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.] -phenyl] -methanesulfonamide, 195 1- (2-. {2- 2- (4- chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.] - phenyl] -ethanone, 196 1- (2- { 2- [2- (4-Chloro-phenyl) -cyclopropyl-H-benzimidazol-5-yl.} - phenyl] -ethanol ^ 197 N- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzyldazol-5-yl.} - phenyl) - methanesulfonamide, 198 2- (2- { 2- [2- (4-chloro-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan- 2-ol, 199 2-. { 2- [2- (4-chloro-pheny] -cyclochlor] -1 H-benzyldazol-5-yl} - benzenesulfonamide, 200 N- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -C, C, C-trifluoro-methanesulfonamide, 201 1- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl}. l) - ethanone, 202 1- (2- { 2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl ) - ethanol, 203 N- (2- { 2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1 H -benzyltriazol-5-yl.} - phenyl ) - methanesulfonamide, 204 2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzyldazole-5-yl. l) - propan-2-ol, 205 2-. { 2- [2- (4-methanesulfonyl-phenol) -cyclopropyl] -1H-benzyldazol-5-yl} - benzenesulfonamide, 206 C> C, C-trifluoro-N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzyldazole-5-yl.} -phenol ) -metanesulfonamide, 207 1 - [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H-benzyl midazol-5-yl) -phenyl] -ethanone, 208 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl ] -cyclopropyl.} -1 H -benzimidazol-5-yl) -phenyl] -ethanol, 209 N- [2- (2-. {2- 2- (2.2.2 -trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 210 2- [2- ( 2- {2- (4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl} -cyclopropyl} -1 H -benzylnidazol-5-yl) -phen l] -propan-2-ol, 211 2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H- benzimidazol-5-yl) -benzenesulfonamide, Comp. Name 212 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl.] -1 H -benzylnidazol-5-yl) -phenyl] -methanesulfonamide, 213 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 214 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -ethanol, 215 N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 216 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 217 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 218 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl) .}. -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 219 1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.} -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 220 1- [2- (2-. { . 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H- benzimidazol-5-yl) -phenyl] -ethanol, 221 N- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 222 2- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] - cyclopropyl.} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 223 2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) - phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -benzenesulfonamide, 224 C, C, C-trifluoro-N- [2- (2-. {2- 2- (2.2.3.3, 3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 225 1- (2- { 2- [2- (3-chloro-phenyl ) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, 226 1- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 227 N- (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl}. -phenyl'-methanesulfonamide, 228 2- (2- {.2- [2- (3-Chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-or -229 2-. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 230 N- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.}. -phenyl) -C, C, C-trifluoro methanesulfonamide, 231 1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 232 1 - (2 - { 2- [2- (3-trifluoromethy1-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 233 N- (2- { 2- [2- (3-tnfluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 234 2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 235 2- . { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 236 C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -metanesulfonamide, Comp. Name 237 N- (4- { 2- [5- (2-acetyl-pheny] -1 H-benzyldazol-2-yl] -cyclopropyl. l) -methanesulfonamide, 238 N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] - methanesulfonamide, 239 N- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H-benzimidazol-5-yl} - phenyl ) -metanesulfonamide, 240 N- [4- (2- { 5- [2- (1-Hydroxy-1-methy1-etl) -phenyl] -1 H -benzimidazole-2- 1.} - c-chloropropyl) -phenyl] -methanesulfonamide, 2-1. { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 242 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazole-5 -yl.}.-phenyl) -methanesulfonamide, 243 N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -c clopropyl.}.-phenyl) -C, C, C-trifluoromethanesulfonamide, 244 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy) etl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, 245 C, C, C-trifluoro-N- (4-. {2 - [5- (2-methanesulfonyllamine-phenol) -1 H-benzyldazol-2-yl] -cyclopropyl] -phenyl) -methanesulfonamide, 246 C, C, C-Trifluoro-N- [4- (2-. {5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl}. -cyclopropyl) -phenyl] -methanesulfonamide, 247 2-. { 2- [2- (4-Trifluoromethanesulfonyllamino-pheny] -cyclochlor] -1 H-benzyldazol-5-yl} -benzenesulfonamide, 248 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethanesulfonyl-pheny] -cyclopropyl] -1H-benzimidazole-5-yl. l.}. phenyl) -methanesulfonamide, 249 2- [2- (4-trifluoromethoxy-phenletin) -1 H-benzimidazol-5-yl] -benzenesulfonamide, 250 2- [2 - (4-Trifluoromethyl-phenylethyl) -1H-benzimidazol-5-yl] -benzenesulfonamide, 251 2- [2- (4-trifluoromethanesulfonyl-phenylethyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 252 C, ClC-trifluoro-N-. { 2- [2- (4-trifluoromethoxy-phenylethyl) -1 H -benzimidazol-5-yl] -phenyl-methanesulfonamide, 253 C, C, C-trifluoro-N 2- [2 - (4-trifluoromethyl-phenylethyl) -1 H-benzimidazol-5-yl] -phenyl-methanesulfonamide, 254 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenolletyl] -1 H- benzimidazol-5-yl] -phenyl} -metansulfonamida, 255 1-. { 2- [2- (4-chloro-phenylethenol) -1 H-benzimidazol-5-yl] -phenyl} -etanona, 256 1-. { 2- [2- (4-Chloro-phenylethenyl) -1 H-benzyldazol-5-yl] -phenyl} -ethanol, 257 N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 258 2-. { 2- [2- (4-Chloro-phenylethyl] -1 H-benzimidazol-5-yl] -phenyl} -propan-2-ol, 259 2- [2- (4-chloro-phenylalkyl) -1 H-benzimidazol-5-yl] -benzenesulfonamidal 260 N-. { 2- [2- (4-Chloro-phenyletinyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-trifluoromethanesulfonamide, 261 1-. { 2- [2- (4-methanesulfonyl-phenyletyl) -1 H-benzimidazol-5-yl] -phenyl} -etanone, 262 1 -. { 2- [2- (4-methanesulfonyl-phenolletyl) -1H-benzimidazol-5-yl] -phenyl} -ethanol, 263 N-. { 2- [2- (4-methanesulfonyl-phenylethyl) -1H-benzyldazol-5-yl] -phenyl} - methanesulfonamide, 264 2-. { 2- [2- (4-methanesulfonyl-phenyletinyl) -1 H-benzimidazol-5-yl] -phenyl} -propan-2- ol, Comp. Name 265 2- [2- (4-Methanesulfonyl-phenletin] -1 H-benzimidazol-5-yl] -benzenesulfonamide, 266 C, CIC-trifluoro-N-. { 2- [2- (4-methanesulfonyl-phenolletyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 267 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethy1-ethoxy) -phenylethynyl] -1H-benzimidazole-5-yl. phenyl) -ethanone, 268 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethyl] -1 H- benzamdazol-5-yl.} - phenyl) -ethanol, 269 N- (2- {2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) - phenyletinyl] -1 H- benzimidazpl-5-yl.} - phenyl] -methanesulfonamide, 270 2- (2-. {2- 2- [4- (2,2,2-trifluoro-1-tr Fluoromethyl-ethoxy) -phenethyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 271 2-. { 2- [4- (2.2 I2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -1-H-benzimidazol-5-yl} -benzenesulfonamide, 272 C, C, C-trifluoro-N- (2-. {2- 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenolletyl] - 1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 273 1- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenethyl] -1H -benzimidazol-5-yl.] - phenyl] -ethanone, 274 1- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenolletil] - 1H-benzimidazole-5-yl.] -phenyl] -ethanol, 275 N- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenol L] -1 H-benzimidazol-5-yl.] -phenyl] -methanesulfonamide, 276 2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) - phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl] -propan-2-ol, 277 2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenethyl] -1 H-benzimidazole-5-yl} - benzenesulfonamide, 278 C, C, C-trifluoro-N- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethyl] -1 H- benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, 279 1- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy!) -phenylethyl] -1H-benzamidazole-5! l.}.-phenyl] -ethanone, 280 1- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenethyl] -1H-benzyl midazol-5-yl.} - phenyl) -ethanol, 281 N- (2. {2- 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenylethyl] -1H-benzimidazole -5-! L.].-Phenyl] -metanesulfonamide, 282 2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenethyl] -1 H-benzyldazol-5-yl.) - phenyl] -propan-2-ol, 283 2-. { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 284 C, C, C-trifluoro-N- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenethyl] -1 H - benzimidazol-5-yl.} - phenyl] -methanesulfonamide, 285 1-. { 2- [2- (3-Chloro-phenylethynyl) -1 H -benzyldazol-5-yl] -phenyl} -etanona, 286 2-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 287 N-. { 2- [2- (3-Chloro-phenylethyl) -1 H-benzimidazol-5-yl] -phenyl} - methanesulfonamide, 288 1-. { 2- [2- (3-chloro-phenylethyl] -1 H-benzimidazol-5-yl] -phenyl} Ethanol, 289 2- [2- (3-Chloro-1-n-nilene) -1 H-benzimidazol-5-yl] -benzenesulfonamide, 290 N-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-tnfluoro-methanesulfonamide, 291 1-. { 2- [2- (3-trifluoromethyl-phenylethenyl) -1 H-benzimidazol-5-yl] -phenyl} -etanone, Comp. Name 292 1-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzyrylcylazol-5-yl] -phenyl} -ethanol, 293 N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} - methanesulfonamide, 294 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} -propan-2-ol, 295 2- [2- (3-tnfluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 296 C, C, C-trifluoro-N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 297 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} - methanesulfonamide, 298 N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl} -phenyl) -methanesulfonamide, 299 N- . { 2- [2- (4-methanesulfonylamino-phenylethynyl) -H-benzimidazol-5-yl] -phenyl} - methanesulfonamide, 300 N- (4-. {5- [2- (1-Hydroxy-1-methylene-ethyl) -phenyl] -1H-benzyldazole-2-yl -ethylene] -phenyl) -methanesulfonamide, 301 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 302 C, C, C-trifluoro- N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 303 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -C, C, C-trifluoromethanesulfonamide, 304 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazole-2 -yl-ethynyl}. phenyl) -methanesulfonamide, 305 C>. C, C-tnfluoro-N-. { 4- [5- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -metanesulfonamide, 306 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl .}.-phenyl'-methanesulfonamide, 307 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 308 C, C, C-trifluoro-N 2- [ 2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 309 (E) -N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 310 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 31 (E) -2-hydroxy-1 - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. phenyl) -ethanone, 312 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 314 (E) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 315 (E) -2-. { 2- [2- (4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 316 (E) -2-. { 2- [2- (3,4-dichloro-pheny!) - vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 317 (£) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 318 (£) -2-. { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, Comp. Name 319 (E) -2-. { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 320 (E) -2-. { 2- [2- (2-fluoro-4-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 321 (£) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 322 (£) -2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl] -v] n-1] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 323 (£) -N-methyl-2-. { 2- [2- (2.3.4-trifluoro-phenyl] -v] nl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 324 (£) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 325 (£) -2-. { 2- [2- (2,3-d.fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 326 (E) -2-. { 2- [2- (2,5-d.fluoro-phenyl] -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 327 (E) -2-. { 2- [2- (2,6-difluoro-phenyl) -v-n-1] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 328 (£) -2-. { 2- [2- (3,5-difluoro-pheny] -vinyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, 329 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) in!] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 330 (E) -2-. { 2- (2- (4-fluoro-2-trifluoromethyl-phenyl) inyl] -1 H -benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, 331 (E) -2-. {2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, 332 (£) -2- { 2- [2 - (2-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - N -methyl-benzenesulfonamide, 333 (£) -2-. {2- 2- [2- ( 3,5-bis-trifluoromethyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl.} - N -methyl-benzenesulfonamide, 334 (E) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 335 (£) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 336 (E) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 337 (E) -2-. { 2- [2- (2,4-dichloro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 338 (E) -2-. { 2- [2- (3-bromo-pheny] -vinyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 339 (£) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 340 (£) -2-. { 2- [2- (4-Chloro-2-methanesulfonyl-phenyl) -vinyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 341 (£) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenol) -v-n-1] -1H-benzyldazole-5-l} -benzenesulfonamide, 342 (£) -N-methyl-2-. { 2- [2- (4-trifluoromethanesulfonyl-pheny] -vinyl] -1 H -benzyldazole-5-yl} -benzenesulfonamide, Comp. Name 343 (£) -N-methyl-2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 344 (£) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 345 (-r) -N-methyl-2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 346 (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 347 (£) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 348 (£) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 349 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 350 N-methyl-2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 351 (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 357 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 358 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 359 (£) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 360 (£) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 361 (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 362 (£) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 363 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 364 (£) -2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 365 (£) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 366 (£) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 367 (£) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 368 (£) -2-. { 2- [2- (2-Luoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzyzidazol-5-yl} - benzenesulfonamide, 369 (£) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 370 (E) -2-. { 2- [2- (2.3.4-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 371 (E) -2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 372 (£) -2-. { 2- (2- (2,6-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, Compound Name 373 (£) -2- { 2- [2- (3.5 -bis-trifluoromethyl-phenyl) -vinyl] -1H-benzamidazol-5-yl.} - benzenesulfonamide, 374 (£) -2- { 2- [2- (2.5 -bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 375 (E) -2- { 2- [2- ( 4-chloro-2-methanesulfonyl-phenyl) -v-n-1] -1 H-benzimidazol-5-yl.] - benzenesulfonamide, 376 () -2-. {2- 2- [2- ( 3-bromo-phenyl] -v] nyl] -1 H -benzyldazol-5-yl.} - benzenesulfonamide, 378 (£) -2- { 2- [2- (4- chloro-3-trifluoromethyl-phenyl) -v, nl] -1 H -benzyldazol-5-yl.} - benzenesulfonamide, 379 (E) -2-. {2- 2- [2- ( 5-bromo-2-fluoro-phenyl] -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 380 (£) -2- { 2- [2- (4 -trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.] - benzenesulfonamide, 383 2- { 2- [2- (4-fluoro-3-tr fluoromethy1-pheny1) -ethyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 384 2- { 2- [2- (2.3.4-trifluoro-phenyl) - etl) -1 H-benzimidazol-5-yl.} - benzenesulfonamide, 385 2-. { 2- [2- (2,4,5-trifluoro-phenyl) -et'yl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 386 2-. { 2- [2- (2,6-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamida, 387 2-. { 2- [2- (3,5-bis-trifluoromethyl-pheny] -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 388 2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 389 2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 390 2-. { 2- [2- (4-chloro-3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 391 2-. { 2- [2- (3-trifluoromethoxy-pheny] -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 392 2-. { 2- [2- (2,4-d-fluoro-phenyl] -etl] -1 H-benzimidazol-5-yl} -benzenesulfonamide, 393 2-. { 2- [2- (3,4-d.fluoro-phenyl) -etl] -1 H -benzimidazole-5-yl} -benzenesulfonamida, 394 2-. { 2- [2- (2,3-d.fluoro-phenyl) -ethyl] -1H-benzyldazole-5-yl} -benzenesulfonamida, 395 2-. { 2- [2- (2,5-d.fluoro-phenyl) -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamida, 396 2-. { 2- [2- (3,5-difluoro-phenyl) -etl] -1 H-benzimidazole-5-yl} -benzenesulfonamide, 397 2- (2-phenethyl-1H-benzimidazol-5-yl) -benzenesulfonamide, 398 (E) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 400 N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 402 2-. { 2- [2- (2-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 404 2-. { 2- [2- (4-fluoro-2-trifluoromethyl-phenol) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 405 2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 406 (E) -N- (2- { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 407 (£ ) -N- (2- { 2- [2- (4-isopropyl-phenol) -v, nl] -1 H-benzyldazole-5-yl. .-pheny] - methanesulfonamide, 408 (£) -N- (2- { 2- [2- (3-chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl. .}.-phenyl) -methanesulfonamide, 409 (E) -N- (2- { 2- [2- (3-bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, 410 (E) -N- (2- {2- [2- (4-difluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -methanesulfonamide, 411 (E) -N- (2- {2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -methanesulfonamide, 412 (E) -N-. { 2- [2- (2-p-tolyl-vinyl) -1 H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 413 (E) -N- (2- { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl.}. -phenymethanesulfonamide, 414 (E) -N - (2- { 2- [2- (4-ethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 415 (£) -N-. { 2- [2- (2-naphthalen-2-yl-vinyl) -1H-benzimidazol-5-yl] -phenyl} - methanesulfonamide, 416 (E) -N- (2- {2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 417 (£) -N- (2- {2- [2- (3-fluoro-4-tnfluoromethyl-phenyl) -vinyl] - H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 418 ( £) -N- (2- {2- [2- (2-fluoro-4-trifluoromethyl-phenyl) -vinyl] - H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 419 2- . { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 420 2-. { 2- [2- (4-Fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 421 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 422 (E) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 423 (E) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 424 (£) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 425 (E) -2-. { 2- [2- (3-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 426 (£) -2- (2-styryl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 427 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -v-n-1] -1 H-benzyldazole-5-yl} - benzenesulfonamide, 428 (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 429 (£) -2-. { 2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 430 (£) -2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 431 (E) -2-. { 2- [2- (3-Chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 432 (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -H-benzimidazol-5-yl} - benzenesulfonamide, 433 (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, Comp. Name 434 (E) -2-. { 2- [2- (4-Fluoro-phenyl) -vinyl] -H-benzimidazol-5-yl} - benzenesulfonamide, 435 (£) -2-. { 2- [2- (4-difluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 436 (£) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 437 (E) -2-. { 2- (2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 438 (£) -2- { 2- [2- (2-chloro- 6-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 439 (E) -2- { 2- [2- (3-bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 440 (£) -2- { 2- [2- (4-ethoxy-phenyl) -vinyl] -1H-benzimidazole-5 -yl.}. -benzenesulfonamide, 441 (E) -4-fluoro-2-. { 2- [2- (4-trifluorornethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 442 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 443 (£) -N- (2- {3-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -3H-benzimidazol-5-yl} - phenyl) -methanesulfonamide, 444 (£ -4-trifluoromethyl-2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl] -benzenesulfonamide, 445-trifluoromethyl-2 - { 2- [2- (4-Trifluoromethyl-phenyl) -etl] -1 H -benzamidezol-5-yl.} - benzenesulfonamide, 446 (£) - 5-trifluoromethyl-2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzylnidazol-5-yl] -benzenesulfonamide, 447 5-trifluoromethyl-2-. {2 - [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 448 (E) -1- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -vinyl) -phenyl] -ethanone, 449 (E) -2- { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl.}. -propan-2-ol, 450 (/ r) -N-isopropyl-4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} - benzamide, 451 (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 452 (£) -N- (4-. {2- 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) - acetamide, 453 Acid (£) -4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} - benzoic 454 (£) -2-. { 2- [2- (1 H-indol-6-yl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 455 (£) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 456 (£) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 457 N- (2-. {2- 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, 458 (E) -2.2,2-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -acetamide , 459 (E) -2,2,2-trifluoro-ethanesulfonyl acid (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenyl) -amide, Comp. Name 460 (E) -2.2-dimethyl-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl} -phenol ) -propionamide, 461 (2- { 2- [2- (4-trifluoromethyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl}. -phenyl) -am (£) -ethanesulfonic acid, 462 ethyl ester of (E) - (2- {2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. .phenyl) -carbamic acid, 463 (£) -2- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -propan-2-ol, 464 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl}. -phenyl) -propan - 2-ol, 465 (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -fenilamin 466 Ethyl ester of (E) -2- acid. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzoic acid, 467 N- (2- { 2- [2- (4-trifluoromethyl-phenol) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 468 ( E) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 469 (Z) -2- (2-. {2- 2- [ 2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 470 (E) -5- (2-aminosulfonylamino-phenyl) -2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 471 2- (2 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}-phenyl) -propan-2-ol, 472 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyzidazol-5-yl} -phenol, 473 (2- {2- [2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl} -carbamic acid tert-butyl ester, 474 (2- {.2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl}. Phenyl) -methanol, 475 (£) -N-. { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} methanesulfonamide, 476 (£) - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, 477 (E ) -N- (2- { 1 -methyl-2- [2- (4-trifluoromethyl-M-phenyl) -methanesulfonamide, 478 (E) -N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -acetamide, 479-tert-butyl ester of (E) - (2- {. 2- [2- 2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -carbamic acid, 480 (E) -5- (2-methylsulphanyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 481 (£) -2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -5- (2-trifluoromethyl-phenyl) -1 H- benzimidazole, 482 (E) -2- (2- { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol, 483 (E) -dimethyl- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzyl) -amine, 484 ( .E) -2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzaldehyde, 485 (E) -methyl- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H-benzim idazol-5-il} - benzyl) -amine, Comp. Name 486 2-. { 2- [2- (4-trifluoromethyl] -phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzylarriine, 487 (£) -5- (2-trifluoromethyl-phenyl) -2- [2- (4-trifluoromethyl-pheny] -vinyl] -1H-benzimidazole, 488 (£) - 5- (2-trifluoromethoxy-phenyl) -2- [2- (4-trifluoromethyl-pheny] -vinyl] -1 H -benzimidazole, 489 2- [2- (2-phenylethyl- 1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 490 2- (2-phenylethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 491 (E) -5 - (2-aminosulfonylamino-methylphenyl) -2- [2- (4-trifluoromethyl-phenyl) -vini ^ 1 H -benzimidazole, 492 2-. { 2- [2- (4-trifluoromethyl] -phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 494 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H -benzimidazole-5-yl.} -phenyl) -propan- 2-ol, 497 2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl ) - propan-2-ol, 498 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzamide, 499 N-ter-butl-2-. { 2- [2- (4-Trifluoromethyl-phenyl] -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 500 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole, 501 2- (2- {2 - [(1 R , 2R) -2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl] -propan-2-ol, 502 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 503 2- (2- {2 - [(1 S, 2S) -2- (4-trifluoromethyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl}-phenyl) -propan-2-ol, 504 2-. { 2 - [(1 S, 2 S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-?? } - benzenesulfonamide, 505 2- (2- (2 - [(1 S.2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl-1 H-benzimidazol-5-yl] -phenol) -propan-2-ol, 506 2- {2 - [(1 R, 2S) -2- (4-trifluoromethyl-pheny1) -cyclopropyl] -1H-benzyldazole-5 il.) - benzenesulfonamide, 507 2- (2- { 2 - [(1 R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H- benzamidazol-5-yl.} - phenyl) -propan-2-ol and 508 2- {2 - [(1 S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl) l] -1H-benzimidazol-5-yl.} - benzenesulfonamide.
A representative compound of Formula (I) or a form of same includes a compound selected from the group consisting of: Comp. Name 1 (E) -1- (2- { 2- [2- (4-tert-butyl-phenyl] -v] nyl] -1 H -benzimidazole-5-yl. phenyl) - ethanone, 2 (£) -1- (2- { 2- [2- (4-tert-butyl-phenyl) -v] nyl] -1 H -benzyldazole-5-yl}-phenyl) -ethanol, 3 (£) -2-. { 2- [2- (4-tert-butyl-phenol) -vinyl] -1 H-benzimidazol-5-yl} -phenol, 4 (£) -N- (2- { 2- [2- (4-tert-butyl-phenyl] -vinyl] -1H-benzimidazol-5-yl. -fenl) -acetamide, 5 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} - benzamide, 6 (£) -3-. { 2- [2- (4-tert-Butyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} - benzamide, 7 (E) -4-. { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzyldazole-5-yl} benzamide, 8 (E) -N- (4- { 2- [2- (4-tert-butyl-phenyl) -v] n-1] -1 H-benzimidazole-5-yl}-phenyl) -acetamide, 9 (£) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzamidazole- 5-yl.}.-Phenyl) -methanesulfonamide, (E) - (2. {2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-tert-butyl ester - benzimidazol-5-yl.} - phenyl] -carbamic, 11 (£) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl) -1 H -benzimidazol-5-yl} phenylamine, 12 (E) - (2-. {2- [2- (4-tert-butyl-phenyl] -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, 13 (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} - benzamide, 14 (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl] -v] nyl] -1H-benzimidazole-5-yl} -phenol, (E) -1- (2- { 2- [2- (4-Trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, 16 (E) -1- (2. {2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H-benzyl-2-azole; l.} - phenol) -ethanol, 17 (£) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazole-5 -yl.}. - phenyl) -methanesulfonamide, 18 (-E) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 19 (£) -2-. { 2- [2- (4-trifluoromethoxy-pheny] -vinyl] -1H-benzimidazol-5-yl} benzamide, 20 (E) -1- (2- { 2- [2- (4-trifluoromethoxy-pheny] -v] nyl] -1 H -benzimidazole-5-yl. phenyl) -ethanone, 21 (Z) -1- (2. {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -ethanol, 22 (E) -N- (2-. {2- 2- [2- (4-trifluoromethoxy-phenyl) -v] n-1] -1H-benzimidazol-5-yl .}. - phenyl) -methanesulfonamide, 23 (E) -2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazole-5 - l.}. - phenyl) -propan-2-ol, Comp. Name 24 (E) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -v-n-1] -1 H -benzimidazole-5-yl.} -phenyl ) - acetamide, 25 (E) -N- (3- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide , 26 (£) -2-. { 2- [2- (3,4-d.fluoro-pheny] -vinyl] -1 H -benzyldazole-5-yl} - benzamide, 27 (E) -1- (2- { 2- [2- (3,4-difiuoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl ) - ethanone, 28 (E) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -v] nyl] -1 H -benzyldazole-5-yl. .phenyl) -methanesulfonamide, 2-. { 2- [3- (4-tert-Butyl-phenyl) -propyl] -1H-benzimidazol-5-yl} -phenol, 2- [3- (4-tert-butyl-phenyl) -propyl] -5-m-tolyl-1H-benzimidazole, 31 N- (2-. {2- [2- 2- (4-trifluoromethyl-phenol) -ethyl] -1H-benzyldazol-5-yl.] - phenyl] -methanesulfonamide, 2-. { 2- [2- (4-tert-butyl-phenyl) -etl] -1 H-benzimidazole-5-yl} -phenol, 33 3-. { 2- [2- (4-tert-Butyl-pheny] -ethyl] -1 H -benzimidazol-5-yl} -phenol, 34 4-. { 2- [2- (4-tert-butyl-phenyl) -etl] -1 H -benzyldazole-5-yl} -phenol, 35 (E) - (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl.} -phenyl) -metanol, 36 (£) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenol, 37 (E) -N- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl] -vinyl] -1H-benzyldazole-5-yl}-phenyl) -acetamida, 38 (£) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzamide, 39 (E) -1- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl.} .-phenyl) -ethanone, 40 (£) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-pheny] -v] nyl] -1 H -benzimidazole-5 -l.}. -phenyl) -ethanone, 41 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, 42 (£) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzyldazole-5-yl. phenyl) -methanol, 43 (E) -N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazole-5-yl}. phenyl) -acetamide, 44 (£) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl] -vinyl] -1H-benzyldazole-5-l} -benzamide, 45 (E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenol) -v-n-1] -1H-benzamidazol- 5 -l.}.-Phenyl] -ethanol, 1- (2. {2- [2- (4-trifluoromethanesulfonyl-pheny] -eti] -1 H-benzimidazole- 5-alkyl) -phenyl) -ethanol, 47 (E) -2- (2-. {2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 48 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl] -vinyl] -6-trifluoromethyl-1H-benzyl-imidazol-5-yl} -phenol, Comp. Name 49 (eE -3- { 2- [2- (4-tert-butyl-phenyl) -v-n-1] -6-trifluoromethyl-1H-benzamidezol-5 -I-J-phenol, 50 (£) -N- (2- { 2- [2- (4-tert-butyl-phenyl] -v] nyl] -6-trifluoromethyl-1 H-benzimidazole-5 -l.}.-Pheny] -acetamide, 51 (E) - (2- { 2- [2- (4-tert-butyl-phenyl) -v] nyl] -6-tr Fluoromethyl-1 H-benzamdazol-5-yl.] - phenyl) -methanol, 52 (E) -2- [2- (4-tert-butyl-phenyl) -vinyl] -5- ( 2-fluoro-phenyl) -6-trifluoromethyl-1H-benzimidazole, 53 (E) -2-. {2- 2- [2- (4-tert-butyl-pheny] -vinyl] -6-trifluoromethyl ester l-1 H-benzimidazol-5-yl.}. -benzamide, (tert-butyl) ester of (£) - (2- { 2- [2- (4-tert-butyl-phenyl) - vinyl] -6- trifluoromethyl-1 H-benzimidazol-5-yl.] -phenyl] -carbamic acid, 55 (E) -N- (2-. {2- 2- [2- ( 4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 56 (E) -N- (2-. {6-Trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazole-5 -yl.}.-phenyl) -acetamide, 57 (£) -1- (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H - benzimidazol-5-yl.} - phenyl) -ethanone, 58 (E) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -v-nil ] -1H-benzimidazol-5-yl.} - phenyl) -methanol, 59 (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl] -v] nyl] -1 H -benzyldazol-5-yl} -phenol, 60 (E) -3-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl] -v] nyl] -1H-benzyldazole-5-l} -phenol, 61 (E) - (2-. {6-fluoro-2- [2- (4-tr'ifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}-phenyl) -methanol, 62 (£) -1- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole- 5-.l.] - phenyl] -ethanone, 63 (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazole-5-l} -benzamide, 64 (E) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} .phenyl) -acetamide, 65 (E) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H - benzamidazol-5-yl.} - phenyl] -methanesulfonamide, 66 (E) - (2-. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v L] -1 H-benzyldazol-5-yl] -phenyl) -methanol, 67 (£) -1- (2- {6-chloro-2- [2- (4-trifluoromet L-phenyl) -vinyl] -1 H -benzimidazol-5-yl.] - phenyl] -ethanone, 68 (E) -2-. { 6-Chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-l} -phenol, 69 (E) -2-. { 2- [2- (4-trifluoromethoxy-phenyl] -v-n-1] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 70 (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzyldazole-5-yl} - benzenesulfonamide, Comp. Name 71 (£) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazole-5-IJ-benzenesulfonamide, 77 () -N- (2-. {2- 2- (4-chloro- fenii) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 78 (£) -2- (2- { 2- [2- (4-chloro-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 79 (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 83 (E) -N- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, (E) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 85 (£) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 95 (E) -N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazole-5-yl ) -phenyl] -methanesulfonamide, 101 (E) -N- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -vinyl.} -1 H - benzimidazol-5-yl) -phenyl] -methanesulfonamide, 113 (E) -N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl .}. - phenyl) -methanesulfonamide, 114 (£) -2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. .phenyl) -propan-2-ol, 129 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -H-benzimidazol-5-yl} - benzenesulfonamide, 130 2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 131 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 139 2-. { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 145 2-. { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 175 2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 190 2-. { 2- [2- (4-tnfluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 198 2- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 234 2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 250 2- [2 - (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 294 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - propan-2-ol, Comp. Name 295 2- [2- (3-Trifluoromethyl-phenletin) -1 H-benzimidazol-5-yl] -benzenesulfonamide, 309 (E) -N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl) -1 H -benzimidazol-5-yl} -benzenesulfonamide, 310 (E) -N-methyl-2-. { 2- [2- (4-Trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazole-5-l} -benzenesulfonamide, 311 (E) -2-hydroxy-1 - (2. {2- [2- (4-trifluoromethyl-phenyl) -vin'yl] -1H-benzimidazol-5-yl}-phenyl] -ethanone, 312 (E) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 314 (E) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 315 (E) -2-. { 2- [2- (4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 316 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 317 (£) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 318 (E) -2-. { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 319 (E) -2-. { 2- [2- (3-fluoro-4-trifluoromethyl-pheny] -vinyl] -1H-benzimidazol-5-l} -N-methyl-benzenesulfonamide, 320 (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 321 (£) -2-. { 2- [2- (3-Chloro-4-fluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 322 (E) -2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl] -v] n-1] -1H-benzyldazol-5-yl} -N-methyl-benzenesulfonamide, 323 (E) -N-methyl-2-. { 2- [2- (2.3.4-trifluoro-phenyl) -vinyl] -1H-benzimidazole-5-l} -benzenesulfonamide, 324 (E) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzyldazole-5-l} -benzenesulfonamide, 325 (E) -2-. { 2- [2- (2,3-difluoro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 326 (E) -2-. { 2- [2- (2,5-d.fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 327 (E) -2-. { 2- [2- (2,6-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 328 (E) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 329 (£) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 330 (£) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, Comp. Name 331 (E) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-l} -N-methyl-benzenesulfonamide, 332 (E) -2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 333 (E) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 334 (E) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 335 (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 336 (E) -2-. { 2- [2- (2-Chloro-6-fluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 337 (£) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 338 (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 339 (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 340 (/ r) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 341 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 342 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 343 (E) -N-methyl-2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-l} -benzenesulfonamide, 344 (£) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1 H -benzyldazole-5-yl} -benzenesulfonamide, 345 (E) -N-methyl-2-. { 2- [2- (4-Trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 346 (E) -2-. { 2- [2- (2-chloro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 347 (E) -2-. { 2- [2- (4-chloro-phenyl] -v] n-1] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 348 (E) -2-. { 2- [2- (2-bromo-pheny] -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 349 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 350 N-methyl-2-. { 2- [2- (3-Trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 351 (E) -2-. { 2- [2- (4-methanesulfonyl-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 357 (E) -2-. { 2- [2- (2,4-d.fluoro-phenyl) -v.n.l] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 358 (£) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 359 (£) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 360 (E) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 361 (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 362 (£) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 363 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 364 (E) -2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 365 (£) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 366 (E) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 367 (£ -2- { 2- [2- (4-fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -benzenesulfonamide, 368 (E) -2- { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl] -vinyl] -1 H -benzimidazol-5-yl}. -benzenesulfonamide, 369 (E) -2- { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 370 (E) -2-. 2- [2- (2,3,4-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 371 (E) -2- { 2- [2- (2.4. 5-trifluoro-phenyl] -vinyl] -1 H -benzimidazol-5-yl.] - benzenesulfonamide, 372 (E) -2- { 2- [2- (2,6-difluoro -phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 373 (E) -2- { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H-benzimidazol-5-yl.} - benzenesulfonamide, 374 (£) -2- { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 375 (£) -2- { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -benzenesulfonamide, 376 (E) -2- { 2- 2- (3-bromine phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 378 (£) -2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 379 (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 380 (.E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, Comp. Name 383 2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl] -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 384 2-. { 2- [2- (2.3.4-trifluoro-phenyl) -ethyl] -1 H -benzimidazole-5-yl} - benzenesulfonamide, 385 2-. { 2- (2- (2,4,5-trifluoro-phenyl) -etl] -1 H-benzimidazol-5-yl.] - benzenesulfonamide, 386 2- { 2- [2- (2,6-d.fluoro-pheny!) -etl] -1 H -benzimidazol-5-yl.] - benzenesulfonamide, 387 2-. {2- 2- [3.5 (bs-) trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 388 2- { 2- [2- (2,5-bis-trifluoromethyl-phenol) -ethyl] -1 H-benzimidazol-5-yl.} - benzenesulfonamide, 389 2-. {2- 2- [2- (4-chloro-2-methanesulfonyl-pheny] -ethyl] -1 H -benzimidazole -5-.l.) - benzenesulfonamide, 390 2- { 2- [2- (4-chloro-3-trifluoromethyl-pheny!) -ethyl] -1H-benzyldazole- 5-yl.) - benzenesulfonamide, 391 2- {2- [2- (3-trifluoromethoxy-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide , 392 2- { 2- [2- (2,4-d.fluoro-pheny!) -ethyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 393 2-. 2- [2- (3,4-d.fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, 394 2- { 2- [2- (2,3-difluoro-phen l) -etl] -1 H-benzimidazol-5-yl.] - benzenesulfonamide, 395 2- { 2- [2- ( 2.5-difluoro-phenyl] -ethyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 396 2-. { 2- [2- (3,5-difluoro-pheny] -ethyl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 397 2- (2-phenethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 398 (E) -N, N-d-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazole-5-l} -benzenesulfonamide, 400 N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 402 2-. { 2- [2- (2-chloro-phenyl] -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 404 2-. { 2- [2- (4-fluoro-2-trifluoromethyl-phenyl) -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 405 2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 406 (E) -N- (2- {2- [2- (4-bromo-phenyl) -vinyl] -1H-benzyldazole-5-yl} -phen L) -methanesulfonamide, 407 (E) -N- (2-. {2- 2- [4 - (4-isopropyl-phenyl] -vinyl) -1H-benzimidazol-5-yl} -phenol) -methanesulfonamide, Comp. Name 408 (E) -N- (2- { 2- [2- (3-chloro-4-fluoro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl. . - phenyl) -methanesulfonamide, 409 (E) -N- (2- { 2- [2- (3-bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide 410 (E) -N- (2- { 2- [2- (4-difluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 411 (£ ) -N- (2- { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 412 (E ) -N-. { 2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 413 (E) -N- (2- {2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 414 (E) -N- (2- {2- [2- (4-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 415 (E) - N-. { 2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 416 (£) -N- (2- {2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 417 (E) -N- (2- { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 418 (E) -N- (2- { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -methanesulfonamide, 419 2-. { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 420 2-. { 2- [2- (4-Fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 421 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 422 (E) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-tnfluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 423 (£) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 424 (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl-benzenesulfonamide, 425 (E) -2-. { 2- [2- (3-ethoxy-phenyl] -v] nyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 426 (E) -2- (2-estinl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 427 (£) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 428 (£) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 429 (E) -2-. { 2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 430 (E) -2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, Comp. Name 431 (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 432 (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 433 (E) -2- [2- (2-naphthalen-2-y1-v1n1) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 434 (E) -2-. { 2- [2- (4-fluoro-pheny] -vinyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 435 (E) -2-. { 2- [2- (4-difluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 436 (£) -2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 437 (E) -2-. { 2- [2- (2,4-dichloro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 438 (£) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -vinyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 439 (E) -2-. { 2- [2- (3-bromo-4-fluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 440 (£) -2-. { 2- [2- (4-ethoxy-phenyl) -vinyl] -1H-benzamidazol-5-yl} - benzenesulfonamide, 441 (£) -4-fluoro-2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzyldazol-5-yl} -benzenesulfonamide, 442 2-. { 2- [2- (4-isopropyl-phenyl] -etl] -1 H-benzimidazole-5-yl} - benzenesulfonamide, 443 (E) -N- (2. {3-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -3H-benzyl-2-yldazole; .}.-phenyl) -methanesulfonamide, 444 (E) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethy1-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 445 4-trifluoromethyl-2-. { 2- [2- (4-Trifluoromethyl-phenyl) -etl] -1 H-benzimidazol-5-yl} -benzenesulfonamide, 446 (£) -5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-pheny] -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 447 5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 448 (E) -1 - [4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. - vinyl) -phenyl) -ethanone, 449 (£) -2-. { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - propan-2-ol, 450 (£) -N-isopropyl-4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} -benzamide, 451 (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 452 (£) -N- (4- { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) -acetamide, Comp. Name 453 Acid (E) -4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl-benzoic acid, 454 (E) -2-. { 2- [2- (1 H-indol-6-yl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 455 (E) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 456 (E) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 457 N- (2- {2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -acetamide, 458 ( E) -2.2,2-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -acetamide, 459 (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (£) -2.2.2-trifluoro- ethanesulfonic acid, 460 (E) -2,2-dimethyl-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -propionamide, (£) -ethanesulfonic acid 2-1- (2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -amide, 462 (E) - (2- {2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl} -carbamic acid methyl ester, 463 ( £) -2- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 464 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl}. -phenyl) -propan-2-ol, 465 (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenylamine, 466 ethyl ester of (E) -2- acid. { 2- [2- (4-trif luoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzoic acid, 467 N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 468 (E ) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 469 (Z) -2- (2-. {2- 2- ( 4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 470 (£) -5- (2-aminosulfonylamino-phenyl) -2- [2 - (4-trifluoromethyl-phenyl) -vinyl] -H-benzimidazole, 471 2- (2-. {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - phenyl) -propan-2-ol, 472 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - phenol, (2- {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H-benzimidazole-5-yl} -phenyl} -carbamic acid tert-butyl ester , 474 (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, 475 (E) -N-. { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 1 Comp. Name 476 (E) - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] - H -benzimidazol-5-yl.} - phenyl) -methanol, 477 (E) -N - (2- { 1-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl] -methanesulfonamide, 478 (E) -N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, 479-tert-butyl ester of (£) - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl} -carbamic acid, 480 (£) - 5- (2-Methylsulfanyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 481 (E) -2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl ] -5- (2-trifluoromethyl-phenyl) -1 H -benzimidazole, 482 (E) -2- (2- { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole -5-yl.} - phenyl) -propan-2-ol, 483 (£) -dimethyl- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole -5-yl.}. -benzyl) -amine, 484 (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzaldehyde, 485 (E) -methyl- (2- {2- [2- (4-trifluoromethyl-phen-benzyl) -amine, 486 2- {2- [2- (4-trifluoromethyl-phenyl)} ) -ethyl] -1 H-benzimidazol-5-yl.} - benzylamine, 487 (£) -5- (2-trifluoromethyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] - 1 H- benzimidazole, 488 (E) -5- (2-trifluoromethoxy-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 489 2- [2- (2- phenylethynyl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 490 2- (2-phenylethynyl-1 H -benzimidazol-5-yl) -benzenesulfonamide, 491 (E) -5- (2 -aminosulfonylamino-methylphenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole, 492 2- { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazole -5-yl] -phenyl.}. -propan-2-ol, 494 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl .}.-phenyl) -propan-2-ol, 497 2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. ) -propan-2-ol, 498 2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - benzamide, 499 N-tert-butyl l-2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 500 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole, 501 2- (2- {2 - [(1 R , 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, Comp. Name 502 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, 503 2- (2- {2 - [(1 S, 2S) -2- (4-trifluoromethyl-pheny] -cyclopropyl] -1H-benzimidazol-5-yl}-phenyl) -propan-2-ol, 504 2-. { 2 - [(1S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, 505 2- (2- {2 - [(1 S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) - propan-2-ol, 506 2-. { 2 - [(R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 507 2- (2- {2 - [(1 R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenol) -propan-2-ol and 508 2-. { 2 - [(1S, 2R) -2- (4-tnfluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide.
A representative compound of Formula (I) or a form of same includes a compound selected from the group consisting of: Comp. Name 1 (E) -1- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 2 (£) -1- (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanol, 3 (E )-2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenol, 4 (£) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide , 5 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzamide, 9 (E) -N- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 10 ter- butyl ester of (E) - (2 { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -carbamic acid, (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} phenylamine, 12 (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, 13 (-) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, 15 (E) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, 16 ( E) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 17 (£) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, Comp. Name 18 (£) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol , 22 (£) -N- (2- { 2- [2- (4-tnfluoromethoxy-phenyl) -vinyl] - H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 27 (E) -1- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 28 (£) -N- ( 2- {2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 31 N- (2-. {2- 2- [ 2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 34 4-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 35 (_) - (2- { 2- [2- (4-tnfluoromethylsulfanyl-phenyl) -vinyl] -1H-bericimidazol-5-yl.} - phenyl) -methanol, 38 (E )-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, 39 (E) -1- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -ethanone, (E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -ethanone, 41 (E) - 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenol, 42 (£) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, 44 (E )-2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, 45 (E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -ethanol, 1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 47 (E) -2- (2 - { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -propan-2-ol, 50 (/) -N- (2 - { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl}. -phenyl) -acetamide, 51 (E) - (2 - { 2- [2- (4-tert-Butyl-phenyl] -vinyl] -6-trifluoromethyl-1 H-benzyldazol-5-yl} -phenyl) -methanol, 53 (£) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl-benzamide, 56 (E) -N- (2-. {6-trifluoromethyl- 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -acetamide, 58 (E) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanol, 59 (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenol, Comp. Name 61 (£) - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. l) -methanol, 62 (E) -1 - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, 63 (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl} benzamide, 66 (E) - (2-. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazole-5-yl. - phenol) -methanol, 67 (E) -1- (2. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v] n-1] -1 H- benzamidazol-5-yl] -phenyl) -ethanone, 68 (E) -2-. { 6-Chloro-2- [2- (4-trifluoromethyl-phenyl] -v] nyl] -1 H -benzyldazol-5-yl} - phenol, 69 (E) -2-. { 2- [2- (4-trifluoromethoxy-pheny] -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 70 (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 71 (E) -2-. { 2- [2- (4-Trifluoromethanesulfonyl-phenyl) -v] nl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 77 (E) -N- (2- { 2- [2- (4-chloro-phenyl) -v] n-1] -1 H-benzimidazol-5-yl.}. l) - methanesulfonamide, 78 (E) -2- (2- { 2- [2- (4-chloro-phenyl) -v] nl] -1 H -benzyldazole-5-yl .}. -phenyl) -propan-2-ol, 79 (£) -2-. { 2- [2- (4-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 84 (E) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 -ol, 95 (£) -N- [2- (2- { 2- [4- (2,2,2-tr.fluoro-ethoxy) -phenyl] -v.n.l.} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 114 (Z) -2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - phenyl] -propan-2-ol, 129 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 130 2-. { 2- [2- (4-trifluoromethyl-phenol) -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 131 2-. { 2- [2- (4-Trifluoromethanesulfonyl-pheny] -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 139 2-. { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 175 2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 190 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 198 2- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazole-5-yl.] -phenol) -propan-2 ol, 250 2- [2- (4-trifluoromethyl-phenylethenyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, Comp. Name 294 2-. { 2- [2- (3-trifluoromethyl] -phenylethyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 295 2- [2- (3-trifluoromethy1-phenylethyl) -1 H -benzimidazol-5-yl) -benzenesulfonamide, 309 (E) -N-tert-butyl- 2-. { 2- [2- (4-trifluoromethyl] -phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 310 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 311 (£) -2-hydroxy-1- (2- {2- [2- (4-trifluoromethy1-pheny1) -vinyl] -1H-benzimidazol-5-yl} .-phenyl) -ethanone, 312 (E) -2-. { 2- [2- (4-bromo-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 314 (£) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 315 (£) - 2-. { 2- [2- (4-fluoro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 316 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 317 (E) -2-. { 2- [2- (3-bromo-4-fluoro-phenyl] -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 3 8 (E) -2-. { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 319 (E) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vin] -1-H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 320 (E) -2-. { 2- [2- (2-fluoro-4-trifluoromethy1-pheny1) viny] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 321 (Z) -2-. { 2- [2- (3-Chloro-4-fluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 322 (E) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 323 (JE) -N-methyl-2-. { 2- [2- (2,3,4-trifluoro-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} - benzenesulfonamide, 324 (£) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 325 (E) -2-. { 2- [2- (2,3-difluoro-pheny] -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 326 (E) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 327 (E) -2-. { 2- [2- (2,6-difluoro-pheny] -vinyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 328 (E) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 329 (.) -2-. { 2- [2- (3,4-d.fluoro-pheny] -vinyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, Comp. Name 330 (E) -2-. { 2- [2- (4-fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzyldazol-5-yl} - N-methyl-benzenesulfonamide, 331 (E) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 332 (E) -2-. { 2- [2- (2-Fluoro-3-trifluoromethy1-phenyl) -vinyl] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 333 (E) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 334 (E) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl] -vinyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, 335 (E) -2-. { 2- [2- (3-chloro-2-fluoro-pheny] -vinyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, 336 (E) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 337 (E) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 338 (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1H-benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 339 (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl] -v] nyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, 340 (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} - N-methyl-benzenesulfonamide, 341 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenol) -v, n-1] -1H-benzimidazole-5-yl} -benzenesulfonamide, 342 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl] -v] nyl] -1H-benzyldazole-5-yl} -benzenesulfonamide, 343 (E) -N-methyl-2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 344 (E) -N-methyl-2-. { 2- [2- (3-Trifluoromethoxy-phenyl) -vinyl] -1 H -benzyldazol-5-yl} -benzene sulfonamide, 345 (E) -N-methyl-2-. { 2- [2- (4-tnfluoromethoxy-pheny] -vinyl] -1 H -benzyldazole-5-l} -benzenesulfonamide, 346 (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1H-benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 347 (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 348 (E) -2-. { 2- [2- (2-bromo-pheny] -vinyl] -1H-benzyldazole-5-yl} -N-methyl-benzenesulfonamide, 349 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -v] nl] -1 H-benzimidazol-5-yl} -N-methyl'-benzenesulfonamide, 350 N-methyl-2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 357 (E) -2-. { 2- [2- (2,4-d.fluoro-phenyl] -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 358 (/ E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 359 (£) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 360 (£) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 361 (E) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 362 (E) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 363 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 364 (£) -2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 365 (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 366 (E) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 367 (£) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 368 (E) -2-. { 2- [2- (2-fluoro-3-tnfluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 369 (£) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 370 (£) -2-. { 2- [2- (2.3.4-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 371 (.5) -2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 372 (£) -2-. { 2- [2- (2,6-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 373 (E) -2-. { 2- [2- (3,5-bis-tnfluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 374 (E) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 375 (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 376 (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 378 (E) -2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 379 (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 380 (£) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 383 2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 384 2-. { 2- [2- (2.3.4-trifluoro-phenyl] -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 385 2-. { 2- [2- (2,4,5-trifluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 386 2-. { 2- [2- (2,6-difluoro-phenyl) -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 387 2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -etl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 388 2-. { 2- [2- (2,5-bis-trifluoromethyl-pheny] -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 390 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 391 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 392 2-. { 2- [2- (2,4-d.fluoro-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 393 2-. { 2- [2- (3,4-difluoro-phenyl) -etl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 394 2-. { 2- [2- (2,3-difluoro-phenyl] -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 395 2-. { 2- [2- (2,5-difluoro-pheny] -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 396 2-. { 2- [2- (3,5-difluoro-phenyl) -etl] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 397 2- (2-phenethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 398 (E) -N, N-d-methyl-2-. { 2- [2- (4-trifluoromethy1-phenyl) -vin1] -1H-benzyldazol-5-yl} -benzene sulfonamide, 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 402 2-. { 2- [2- (2-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamida, 404 2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 405 2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 406 (E) -N- (2-. {2- 2- [2- (4-bromo-pheny] -vinyl] -1 H -benzimidazol-5-yl.} - phenol) -methanesulfonamide, 407 (E) -N- (2- {2- [2- (4-isopropyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) - methanesulfonamide, 410 (E) -N- (2- { 2- [2- (4-difluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenol) -metanesulfonamide, 411 (E) -N- (2- {2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. phenyl) -methanesulfonamide, Comp. Name 412 (£) -N-. { 2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 413 (E) -N- (2- {2- [2- (4-dimethylamino-phenyl) -vinyl] - H -benzyl) -5-yl} - phenyl) -metanesulfonamide, 414 (£) -N- (2- {2- [2- (4-ethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) - methanesulfonamide, 415 (£) -N-. { 2- [2- (2-naphthalen-2-yl-v-n-1) -1 H-benzimidazol-5-yl] -phenyl} - methanesulfonamide, 416 (E) -N- (2- { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl ) - methanesulfonamide, 417 (£) -N- (2- { 2- [2- (3-fluoro-4-trifluoromethyl-pheny!) -v! n!] - H-benzimidazole-5! 1.}.-phenyl) -methanesulfonamide, 418 (/ E) -N- (2- {2- [2- (2-fluoro-4-trifluoromethyl-phenyl) -vinyl] -H-benzimidazole-5-} 1.}. - phenyl) -methanesulfonamide, 419 2-. { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H-benzimidazol-5-yl} -benzenesulfonamide, 420 2-. { 2- [2- (4-fluoro-phenyl] -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 421 2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 422 (£) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazole , 423 (£) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 424 (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethy1-pheny1) viny] -1H-benzimidazol-5-yl} - benzenesulfonamide, 426 (£) -2- (2-styryl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 427 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 428 (E) -2-. { 2- [2- (4-chloro-2-fluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 429 (E) -2-. { 2- [2- (4-isopropyl-phenyl] -vinyl] -1H-benzyldazole-5-yl} - benzenesulfonamide, 430 (£) -2- [2- (2-p-tolyl-vinyl) - H-benzimidazol-5-yl] -benzenesulfonamide, 431 (E) -2-. { 2- [2- (3-chloro-2-fluoro-pheny] -vinyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 432 (ZE) -2-. { 2- [2- (3-chloro-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 433 (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 434 (E) -2-. { 2- [2- (4-fluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 435 () -2-. { 2- [2- (4-difluoromethy1-phenyl] -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 436 (E) -2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 437 (£) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 438 (£) -2-. { 2- [2- (2-chloro-6-fluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 439 (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 440 (£) -2-. { 2- [2- (4-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 442 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -1H-benzimidazol-5-?? } - benzenesulfonamide, 444 (E) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 445 4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 446 (£) -5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 447 5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 448 (E) -1- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl) -1H-benzimidazol-2-yl} - vinyl) -phenyl] -ethanone, 449 (E) -2-. { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2- ol, 451 (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 455 (E) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 456 (£) -2-. { 2- [2- (4-Acetyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 461 (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of the acid (E) ) -ethanesulfonyl, 462 methyl ester of (E) - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl ester ) -carbamic, 463 (E) -2- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - propan-2-ol, 464 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol , 465 (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenylamine, 466 Ethyl ester of (E) -2- acid. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzoic acid, 467 N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 468 ( E) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 469 (Z) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -fe-propan-2-ol, Compo.Name 470 (iE) -5- (2-aminosulfonylamino-phenyl) -2- [ 2- (4-trifluoromethyl-phenyl) -vinyl] -1 H-benzimidazole, 471 2- (2-. {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5- il.}. - phenyl) -propan-2-ol, 475 (E) -N- { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl.}. - methanesulfonamide, 476 (£) - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanol, 482 (E) -2- (2- { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol, 489 2- [2- (2-phenylethynyl-1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 490 2- (2-phenylethynyl-1 H-benzimidazol-5-yl) - benzenesulfonamide, 491 (E) -5- (2-aminosulfonylamino-methylphenyl) -2- [2- (4-trifluo romethyl-phenyl) -vinyl] -1H-benzimidazole, 492 2-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 494 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.}. -pheni!) - propan- 2-ol, 497 2- (2- { 2- [2- (4-tnfluoromethoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 498 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzamide, 500 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole, 501 2- (2- {2 - [(1 R , 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 502 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 503 2- (2- {2 - [(1 S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) - propan-2-ol and 504 2-. { 2 - [(1S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide.
A representative compound of Formula (I) or a form of same includes a compound selected from the group consisting of: Comp. Name 1 (E) -1- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 2 (E) -1 - (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, Comp. Name 5 (E) -2-. { 2- [2- (4-tert-butyl-phenyl] -v] nyl] -1H-benzimidazol-5-yl} -benzarnida, 9 (£) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazole-5-yl.} -phenl) - methanesulfonamide, 12 (E) - (2-. {2- 2- [2- (4-tert-butyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl] -phenyl ) - methanol, 16 (Z) -1- (2-. {2- 2- [2- (4-trifluoromethyl-pheny] -v] n-1] -1 H -benzimidazol-5-yl} - phenyl) -ethanol, 17 (E) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzamidazole-5- L.} - phenyl) -methanesulfonamide, 18 (E) -2- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl} -1 H-benzimidazole} -5-.l.) - phenyl) -propan-2-ol, 22 (£) -N- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -v] nyl] -H -benzimidazol-5-yl.} - phenol) -methanesulfonamide, 31 N- (2. {2- 2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, 35 (E) - (2- { 2- [2- (4-trifluoromethylsulfanyl-pheny] -vinyl] -1H-benzyl Dazol-5-yl.} - phenyl) -methanol, 40 (E) -1- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -H -benzimidazol-5-yl.}.-phenyl) -ethanone, 42 (E) - (2- { 2- [2- (4-trifluoromethanesulf nl-phenyl] -vinyl] - H-benzyldazole-5-yl} phenyl) -methanol, 45 (E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -v-n-1] -1H-benzimidazole- 5 - l.} .phenyl) -ethanol, 1- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazole-5-yl} Phenyl) -ethanol, 47 (£) -2- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl} -1H-benzimidazole} - 5-yl.}.-Phenyl) -propan-2-ol, 51 (E) - (2- { 2- [2- (4-tert-butyl-phenyl) -v] nyl] -6- trifluoromethyl-1 H-benzamidazol-5-yl.] - phenyl) -methanol, 53 (E) -2-. { 2- [2- (4-tert-butyl-phenyl) -v-n-1] -6-trifluoromethyl-1H-benzimidazol-5-yl} -benzamide, 58 (E) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl ) -methanol, 61 (E) - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1 H -benzyldazole-5- L.}.-Phenyl) -methanol, 66 (E) - (2-. {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzamidazol-5-yl.) -phenyl] -methanol, 69 (E) -2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 70 (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 71 (£) -2-. { 2- [2- (4-Trifluoromethanesulfonyl-phenyl) -vinyl] -H-benzimidazole-5-l} -benzenesulfonamide, 77 (E) -N- (2- { 2- [2- (4-chloro-pheny] -v] n-1] -1 H-benzimidazole-5-p. 1.}. - pheny!) - methanesulfonamide, Comp. Name 78 (E) -2- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol , 79 (E) -2-. { 2- [2- (4-chloro-phenyl'-vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 84 (E) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 -ol, 114 (E) -2- (2- { 2- [2- (3-tnfluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan -2-ol, 129 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 130 2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 131 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 139 2-. { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 175 2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 190 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-?? } - benzenesulfonamide, 198 2- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 250 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 294 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} - propan-2-ol, 295 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 310 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 311 (/ E) -2-hydroxy-1- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -etanone, 312 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 314 (£) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 315 (E) -2-. { 2- [2- (4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 316 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 317 (Z ^) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 318 (E) -2-. { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, Comp. Name 319 (E) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 320 (£) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 321 (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 322 (E) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl-N-methyl-benzenesulfonamide, 323 (E) -N-methyl-2-. { 2- [2- (2.3.4-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 324 (E) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 328 (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 329 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 331 (E) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 332 (E) -2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 333 (E) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 335 (£) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 337 (Z) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 339 (£) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 340 (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 341 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 342 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 344 (E) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 345 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 347 (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 349 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 350 N-methyl-2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 357 (E) -2-. { 2- [2- (2,4-difluoro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 358 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 359 (E) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 360 (E) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 361 (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 362 (E) -2-. { 2- [2- (3-trifluoromethoxy-pheny!) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 363 (E) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 364 (E) -2-. { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 365 (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 366 (£) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 367 (E) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 368 (E) -2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 369 (E) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl} -benzenesulfonamide, 370 (E) -2-. { 2- [2- (2.3.4-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 371 (£) -2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 372 (E) -2-. { 2- [2- (2,6-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 373 (£) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 374 (E) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 376 (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 378 (E) -2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 379 (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 380 (E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 383 2-. { 2- [2- (4-Fluoro-3-tnfluoromethyl-phenyl) -ethyl] -H-benzimidazol-5-yl} - benzenesulfonamide, 384 2-. { 2- [2- (2,3,4-tnfluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 385 2-. { 2- [2- (2,4,5-trifluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 386 2-. { 2- [2- (2,6-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 387 2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 388 2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 390 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 391 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 392 2-. { 2- [2- (2,4-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 393 2-. { 2- [2- (3,4-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 394 2-. { 2- [2- (2,3-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 395 2-. { 2- [2- (2,5-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 396 2-. { 2- [2- (3,5-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 397 2- (2-phenethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 398 (£) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -eti!] - 1 H-benzimidazol-5-yl} - benzenesulfonamide, 402 2-. { 2- [2- (2-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 404 2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 405 2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 407 (E) -N- (2- {2- [2- (4-isopropyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 417 (£) -N- (2- { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole-5-yl.} -phenyl] - methanesulfonamide, 418 (£) -N- (2- {2- [2- (2-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl ) -metanesulfonamide, 419 2-. { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 420 2-. { 2- [2- (4-Fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 421 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 422 (£) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 423 (£) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 424 (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 426 (E) -2- (2-estinl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 427 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 428 (Z) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 429 (E) -2-. { 2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 430 (E) -2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 431 (£) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 432 (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 433 (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 434 (E) -2-. { 2- [2- (4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 435 (E) -2-. { 2- [2- (4-difluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 436 (£) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -H-benzimidazol-5-yl-benzenesulfonamide, 437 (E) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 438 (Z) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -vinyl) -1 H -benzimidazol-5-yl} - benzenesulfonamide, 439 (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 440 (£) -2-. { 2- [2- (4-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 442 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 444 (E) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 445 4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, Comp. Name 446 (E) -5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 447 5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 448 (E) -1- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. - vinyl) -phenyl] -ethanone, 449 (E) -2-. { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -propan- 2-ol, 451 (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 455 (E) -2-. { 2- [2- (2,4-bis-tnfluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 456 (E) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 461 (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide (£) ) -ethanesulfonic acid, 462 methyl ester of (E) - (2 { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) - Carbamic, 463 (Z) -2- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan- 2-ol, 464 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 466 Ethyl ester of (E) -2- acid. { 2- [2- (4-trifluoromethyl-fentl) -vinyl] -1H-benzimidazol-5-yl} -benzoic acid, 468 (£) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 469 (Z) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] - H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 470 (=) - 5- (2-aminosulfonylamino-phenyl) -2- [2- (4-trifluoromethyl-phenyl] -vinyl] -1 H -benzimidazole, 471 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 475 (E) -N-. { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 476 (E) - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanol, 482 (E ) -2- (2- { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 489 2- [2- (2-Phenylethynyl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 490 2- (2-phenylethynyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, 491 (E ) -5- (2-Aminosulfonylamino-methylphenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 492 2-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - propan-2-ol, 494 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 -ol, Comp. Name 497 2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 498 2-. { 2- [2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyldazol-5-yl} benzamide, 500 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1H-benzimidazole, 501 2- (2- {2 - [(1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyldazol-5-yl}. -phenyl] -propan-2- ol, 503 2- (2- {2 - [(1 S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyldazole-5-yl. phenyl) -propan-2-ol and 504 2-. { 2 - [(1 S, 2 S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide.
A representative compound of Formula (I) or a form thereof includes a compound selected from the group consisting of: Comp. Name 9 (E) -N- (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 12 (E) - (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanol, 17 (E) - N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 18 (E) -2- (2 - { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 69 (E) -2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 70 (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 78 (E) -2- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 -ol, 79 (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 114 (E) -2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan -2-ol, 130 2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 310 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 312 (E) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 319 (E) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, 341 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 357 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 358 (Z ^) - 2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 362 (E) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 369 (£) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 384 2-. { 2- [2- (2.3.4-trifluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 390 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, Comp. Name 391 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 394 2-. { 2- [2- (2,3-d ifl uoro-phen i l) -ethyl] -1 H-benzyldazol-5-yl} - benzenesulfonamide, 398 (E) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzyldazole-5-yl} -benzenesulfonamide, 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 407 (E) -N- (2- {2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl} - methanesulfonamide, 421 2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl] -etl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 422 (£) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl] -v] nyl] -1H-benzimidazole, 428 (E) - 2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 429 (£) -2-. { 2- [2- (4-isopropyl-phenyl) -v] n-1] -1 H-benzimidazol-5-yl} - benzenesulfonamide, 430 (£) -2- [2- (2-p-tolyl-viny) -1H-benzimidazol-5-yl] -benzenesulfonamide, 434 (E) -2-. { 2- [2- (4-fluoro-phenyl] -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 442 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 449 (E) -2-. { 2- [2- (2-quinolin-6-yl-v-n-1) -1 H-benzimidazol-5-yl] -phenyl} -propan-2-ol, 461 (2- { 2- [2- (4-trf) uoromethyl'-phenyl) -viryl] -1H-benzimidazol-5-yl}-pheny] - (E) -ethanesulfonic acid amide, 464 2- (2- { 2- [2- (4-trifluoromethyl-pheny] -eti] -1 H-benz Mdazol-5-yl.} - phenyl] -propan-2-ol, 468 (£) -2- [2- (2-styryl-1H-benzimidazol-5-yl) -phenyl] -propan-2-ol > 469 (Z) -2- (2- { 2- [2- (4-trifluoromethyl-pheny] -vinyl] -1 H -benzyldazol-5-yl.} - phenol ) -propan-2-ol, 471 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazole-5-yl.} - phenyl) -propan -2-ol, 489 2- [2- (2-phenylethenyl-1H-benzyldazol-5-yl) -phenyl] -propan-2-ol, 492 2-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} - propan-2-ol and 503 2- (2- { 2 - [(1 S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5- il.}. -phenyl) -propan-2-ol.
A prophetic representative compound of Formula (I) or a form thereof includes a compound selected from the group consisting in: Comp. Name 72 (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -metanesulfonamide, 73 (E) -C, CIC-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. .-phenyl) -metanesulfonamide, 74 (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazole-5 -yl.}. -phenyl) -methanesulfonamide, 75 (E) -1- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} .-phenyl) -ethanone, 76 (E) -1- (2- {2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanol, 80 (E) -N- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - C, C, C- trifluoro-methanesulfonamide, 81 (£) -1- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) -ethanone, 82 (E) -1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 86 (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 87 (E) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl} - ^ -benzimidazol-5-yl) - phenyl] -ethanone, 88 (£) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl.} -1 H - benzimidazol-5-yl) -phenyl] -ethanol, 89 (E) -N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl.} -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 90 (E) -2- [2- (2- { 2- [4- (2,2,2-trifluoro-1 -trifluoromethyl-ethoxy) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 91 (E) -2- (2-. {2- 2- [4 - (2,2,2-trifluoro-1-trifluoromethyl- ethoxy) -phenyl] -vinyl} -1 H- benzimidazol-5-yl) -benzenesulfonamide, 92 (E) -C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1 -trifluoromethyl-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 93 (E) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} - H-benzimidazol-5-yl) -phenyl] -etanone, 94 (E) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazole-5-yl. ) -phenyl] -ethanol, 96 (^ - ^^^ - ^^^^ - trifluoro-ethoxyHenylJ-vinylJ-I H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 97 (E) -2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl) -benzenesulfonamide, 98 (E) -C , C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H- benzimidazol-5-yl) phenyl] -methanesulfonamide, Comp. Name 99 (E) -1- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -vinyl.} -1 H-benzimidazol-5-yl. ) -phenyl] -ethanone, 100 (£) -1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -vinyl.} -1H- benzimidazol-5-yl) -phenyl] -ethanol, 102 (E) -2- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 103 (E) -2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy ) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl) -benzenesulfonamide, 104 (E) -C, C, C-tnfluoro-N- [2- (2-. {2- 2- [4 - (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -vinyl.} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 105 (E) -1- (2-. {2 - [2- (3-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 106 (£) -1- (2-. {2- 2- [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanol, 107 (E) -N- (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 108 (E) -2- (2- { 2- [2- (3-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.}. -phenyl) -propan-2-ol, 109 (E) -2-. { 2- [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 110 (E) -N- (2- {2- [2- (3-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -C, C , C-trifluoro-methanesulfonamide, 111 (£) -1- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) ethanone, 112 (£) -1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 115 (E) -2-. { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 116 (E) -C, C, C-tnfluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} .-phenyl) -metanesulfonamide, 117 (E) -N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) - methanesulfonamide, 118 (E) -N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -vinyl) - phenyl] -methanesulfonamide, 119 (E) -N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -vinyl) -1 H -benzimidazol-5-yl} phenyl) -metanesulfonamide, 120 (E) -N- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl} - vinyl) -phenyl] -methanesulfonamide, 121 (E) -2-. { 2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 122 (£) -C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1H-benzimidazol-5-yl} .-phenyl) -metanesulfonamide, 123 (E) -N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.}.-phenN) - C, C, C-trifluoro-methanesulfonamide, 124 (E) -C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -fenii] -1 H- benzimidazol-2-yl.}. -vinyl) -phenyl] -methanesulfonamide, Comp. Name 125 (E) -C, C, C-trifluoro-N- (4-. {2- 2- [2- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] - vinyl.}.-phenyl] -methanesulfonamide, 126 (£) -C, C, C-trifluoro-N- [4- (2- { 5- [2- (1-hydroxy-1- methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl.] - vinyl) -phenyl] -methanesulfonamide, 127 (£) -2-. { 2- [2- (4-Trifluoromethanesulfonylamine-phenyl) -v-n-1] -1H-benzamidazol-5-yl} -benzenesulfonamide, 128 (?) - 0.0.0-1 p ???? G? -? - (4- { 2- [5- (2-1p ???? G ???? 3? 5 ??????? 3G ???? -? 6 ???) - 1 H-benzamdazol-2-yl] -vinyl.}.-Phenyl) -methanesulfonamide, 132 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -1H-benzamidezol-5-yl} -phenyl) -methanesulfonam It gives, 133 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -etl} -1 H- benzimidazole-5) -yl.}.-phenyl) -methanesulfonamide, 134 C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -eti ] -1 H- benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 135 1- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazole-5 -yl.}.-phenyl) -ethanone, 136 1- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 137 N- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 138 2- (2-. { 2- [2- (4-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl}. -phenyl) -propan-2-ol, 140 N- (2-. {2 - [2- (4-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} -phenyl] -C, C, C-trifluoro-methanesulfonamide, 141 1- (2-. { 2- [2- (4-methanesulfonyl-pheny] -etl] -H-benzimidazol-5-yl.} - phenyl) -ethanone, 142 1- (2-. {2- [2- (4-methanesulfonyl-pheny] -ethyl] -1 H -benzimidazol-5-yl}. -phenyl] -ethanol, 143 N- (2-. {2- 2- [2 - (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 144 2- (2- { 2- [2- (4-methanesulfonyl- phenol) -ethyl] -1H-benzyldazole-5-yl.} - phenyl] -propan-2-ol, 146 C, C, C-tnfluoro-N- (2-. { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl] -phenyl) -methanesulfonamide, 147 1- [2- (2-. { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -etyl] -1 H-benzimidazol-5-yl) -phenyl] - ethanone, 148 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-e toxy) -phenyl] -ethyl.}. -1H- benzimidazol-5-yl) -phenyl] -ethanol, 149 N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] - etl.) -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 150 2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-tnfluoromethyl- ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 151 2- (2- { 2- [4- (2.2.2 -trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -benzenesulfonamide, 152 C, C, C-tnfluoro-N- [2- (2- {. 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -etyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide , Comp. Name 153 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-ylphenyl] -ethanone, 154 1- [2- (2- { 2- [4- (2, 2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 155 N - [2- (2- { 2- [4- (2,2,2-tnfluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 156 2 - [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2- ol, 157 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 158 C, C , C-trifluoro-N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl} -1-H-benzimidazol-5-yl) -phenyl ] -metanesulfonamide, 159 1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) phenyl] -ethanone, 160 1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazole-5- il) -phenyl] -ethanol, 161 N- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1H-benzimidazole-5 -yl) -phenyl] -methanesulfone measure, 162 2- [2- (2-. { 2- [4- (2.2.3.3, 3-pentaf luoro-propoxy) -f-enyl] -ethyl} - 1 H- benzimidazol-5-yl) -phenyl] -propan-2-ol, 163 2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -ethyl .} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 164 C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2.2.3.3.3-pentafluoro- propoxy) -phenyl] -ethyl-J-H-benzimidazole-Si-phenyl-methanesulfonamide, 165 1- (2- { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazole-5- il.}.-phenyl) -ethanone, 166 1- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 167 N- (2- {2- [2- (3-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 2- (2-. 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 169 2-. { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 170 N- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -C, C, C-trifluoro -methansulfonamide, 171 1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 172 1 - (2 - { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl}. -phenyl] -ethanol, 173 N- (2-. {2- [2- 2- (3-trifluoromethyl-phenyl) -etH] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2- { 2- [2- (3-trifluoromethyl-phenyl) ) -ethyl] -1 H-benzimidazol-5-yl.}. -phenyl) -propan-2-ol, 176 C, C, C-trifluoro-N- (2-. {2- 2- (3 -trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, Comp. Name 177 N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzyldazol-2-yl] -etyl} -phenyl) - methanesulfonamide, 178 N- [4- (2-. {5- [2- (1-Hydroxy-ethyl] -phenyl] -1 H -benzimidazol-2-yl}. etii) -phenyl] -methanesulfonamide, 179 N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 180 N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-et.l) -phenyl] -1 H -benzimidazol-2-yl.} -ethyl) - fenü] -methanesulfonamide, 181 2-. { 2- [2- (4-methanesulfonylamino-pheny] -ethyl] -1 H -benzyldazol-5-yl} - benzenesulfonamide, 182 C, C, C-trifluoro-N- (2-. {2- 2- (4-methanesulfonylamine-phenyl) -etl] -1 H -benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, 183 N- (4. {2-I5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -etl} -phenyl) -C, C, C-trifluoro-methanesulfonamide, 184 C, C, C-tnfluoro-N- [4- (2-. {5- [2- (1-hydroxyl-ethyl) ) -pheny] -1 H-benzimidazole-2-yl.] -ethyl) -phenyl] -methanesulfonamide, 185 C, C, C-trifluoro-N- (4-. { 2- [5- (2-methanesulfonyl-pheny] -1 H-benzimidazol-2-yl] -etyl] -phenyl) -methanesulfonamide, 186 C, C, C-tr fluoro-N- [4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1H-benzamidazole-2 -yl.}.-ethyl) -phenyl] -methanesulfonamide, 187 2-. { 2- [2- (4-Trifluoromethanesulfonylamine-phenyl) -etl] -1 H -benzyldazole-5-l} -benzenesulfonamide, 188 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenylamino) -ethyl} -1H-benzimidazole-5 -yl.}.-phenyl] -methanesulfonamide, 189 2-. { 2- [2- (4-trifluoromethoxy-pheny] -cyclopropyl] -1H-benzyldazole-5-yl} - Benzenesulfonamide, 191 2-. { 2- [2- (4-trifluoromethanesulfonyl-pheny] -cyclopropyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, 192 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. .-phenyl) -methanesulfonamide, 193 C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl. l.}.-phenyl) -methanesulfonamide, 194 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1 H- benzimidazol-5-yl.}. phenyl) -methanesulfonamide, 195 1- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1H-benzimidazole- 5-yl.}.-Phenyl] -ethanone, 196 1- (2- { 2- [2- (4-Chloro-phenyl) -cyclopropyl] -1 H -benzyldazole- 5-yl.}.-Phenyl) -ethanol, 197 N- (2- { 2- [2- (4-chloro-pheny] -cyclopropyl] -1 H -benzyldazole-5- il.}. phenyl) -methanesulfonamide, 199 2-. { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 200 N- (2-. {2- 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzyldazole-5-yl. L) - C, C, C-trifluoro-methanesulfonamide, Comp. Name 201 1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -H-benzimidazol-5-yl.} - phenyl) -ethanone, 202 1- (2-. { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.] - phenol) -ethanol, 203 N- (2- { 2- [2- (4-Methanesulfonyl-phenN) -cyclopropyl] -1 H -benzimidazol-5-yl}. Phenyl) -methanesulfonamide, 2- (2-. {2- 2- ( 4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 205 2-. { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 206 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -phenyl) -methansulfonamide, 207 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} - 1 H-benzimidazol-5-yl ) -phenyl] -ethanone, 208 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl'-cyclopropyl. 1 H-benzimidazol-5-yl) -phenyl] -ethanol, 209 N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl .} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 210 2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) - phenyl] -cyclopropyl.] - 1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 211 2- (2- { 2- [4- (2,2,2-trifluoro-1- tnfluorornethyl-ethoxy-phenyl) -cyclopropyl.] -1 H -benzimidazol-5-yl) -benzenesulfonamide, 212 C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- ( 2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 213 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl.] - H- benzimidazol-5-yl) -phenyl] -ethanone, 214 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 215 N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 216 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -propan-2 -ol, 217 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 218 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} - 1 H-benzimidazol-5-yl) - phenyl] -methanesulfonamide, 219 1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl ) -phenyl] -ethanone, 220 1- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazole-5 -yl) -phenyl] -ethanol, 221 N- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl) ] -cyclopropyl} -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 222 2- [2- (2- { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H- benzimidazol-5-yl) -phenyl] -propan-2-ol, Comp. Name 223 2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 224 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H-benzimidazol-5-yl ) -phenyl] -methanesulfonamide, 225 1 - (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 226 1 - (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-N.}. -phenyl) -ethanol, 227 N- (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 228 2- (2- { 2- [2- (3- chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 229 2-. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 230 N- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.}. -fenN) - C, C, C-trifluoro methanesulfonamide, 231 1- (2-. {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 232 1- (2 - { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 233 N- (2-. {2- 2- [2 - (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 235 2-. { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 236 C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 237 N- (4-. {2- 2- [2- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl}. phenyl) -methanesulfonamide, 238 N- [4 - (2- { 5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-N.} - cyclopropyl) -phenyl-methanesulfonamide, 239 N- (2-. { 2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 240 N- [4- (2-. {5- [2 - (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, 2-1. { 2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 242 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1 H-benzimidazol-5-yl} -phenyl) -methansulfonamide, 243 N- (4- { 2- [5- (2-acetyl-phenyl) -1H-benzimidazol-2-yl] -cyclopropyl.} - phenyl) - C, C, C-trifluoro- methanesulfonamide, 244 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazole-2-yl}. -cyclopropyl) -phenyl] -methanesulfonamide, 245 C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H- benzimidazole- 2-yl] -cyclopropyl.} - phenyl) -methanesulfonamide, Comp. Name 246 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl} -cyclopropyl) -phenyl] -methanesulfonamide, 247 2-. { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1H-benzamidazol-5-yl} -benzenesulfonamide, 248 C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 249 2- [2- (4-trifluoromethoxy-phenylethenyl) -1 H -benzamdazol-5-yl] -benzenesulfonamide, 251 2- [2- (4-tnfluoromethanesulfonyl-phenylethynyl) -1 H-benzimidazol-5-yl] -benzenesulfonamide, 252 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethoxy-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 253 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 254 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 255 1-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanone, 256 1 -. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -ethanol, 257 N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 258 2-. { 2- [2- (4-chloro-phenylethynyl) -H-benzimidazol-5-yl] -phenyl} -propan-2-ol, 259 2- [2- (4-Chloro-phenylethynyl) -1 H -benzucnidazol-5-yl] -benzenesulfonamide, 260 N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C- trifluoro-methanesulfonamide, 261 1-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - Etanone, 262 1 -. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - Ethanol, 263 N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 264 2-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -H-benzimidazol-5-yl] -phenyl} - propan-2-ol, 265 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 266 C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 267 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone , 268 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanol, 269 N- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl}. Phenyl) -methanesulfonamide, 270 2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoron-ylethyl-ethoxy) -phenylethynyl] -H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, Comp. Name 271 2-. { 2- [4- (2,2,2-trifluoro-1-tnfluoromethyl-ethoxy) -phenylethynyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 272 C, C) C-trifluoro-N- (2-. {2- 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl .}.-phenyl) -metanesulfonamide, 273 1- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] - H -benzimidazol-5-yl.} - phenyl) - ethanone, 274 1- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 275 N- ( 2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 276 2- (2-. {2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 277 2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 278 C, C, C-trifluoro-N- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H- benzimidazol-5-yl.} - phenyl) -metanesulfonamide, 279 1- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone , 280 1- (2- { 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.}. -phenyl) -ethanol, 281 N- (2- {2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 282 2- (2- {2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 283 2-. { 2- [4- (2.2.3.3.3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 284 C, C, C-trifluoro-N- (2-. {2- 2- [4- (2.2.3.3,3-pentafluoro-propoxy) -phenylethynyl] -1H-benzimidazol-5-yl}-phenyl) -methanesulfonamide, 285 1-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 286 2-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 287 N-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 288 1-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -ethanol, 289 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 290 N-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C- trifluoro-methanesulfonamide, 291 1 -. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - Etanone, 292 1 -. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -ethanol, 293 N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 296 C, C, C-trifluoro-N-. { 2- [2- (3-Trifluoromethyl-phenylethenyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 297 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} - methanesulfonamide, Comp. Name 298 N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl}. Phenyl) -methanesulfonamide, 299 N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) - H-benzyldazol-5-yl] -phenyl} -methanesulfonamide, 300 N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl} - phenyl) -methanesulfonamide, 301 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 302 C, C, C-tnfluoro-N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 303 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -C, C, C- trifluoro-methanesulfonamide, 304 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzylnidazole-2 -yl-ethynyl}. phenyl) -methanesulfonamide, 305 C, C, C-trifluoro-N-. { 4- [5- (2-methanesulfonylamino-phenyl) -1 H- benzimidazol-2-yl-ethylene] -phenyl} -methansulfonamide, 306 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl -etinyl.}.-phenyl) -methanesulfonamide, 307 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide and 308 C, C, C-trifluoro-N- . { 2- [2- (4-Trifluoromethanesulfonylamino) phenylethyl] -1H-benzimidazol-5-yl] -phenyl} -metansulfonamide.
General Methods of Synthesis Representative compounds of the present invention are can synthesize according to the general methods of synthesis that described below and illustrated in the following schemes. Because that the schemes are a lustracion, the invention should not be interpreted as if limited by chemical reactions and conditions expressed. The preparation of the various starting materials used in the schemes is within the experience of people versed in the art.
The compounds of the present invention can be synthesized by the methods described in the following schemes.
The terms used to describe the invention are used commonly and are known to those skilled in the art. As used in the present memory, the following abbreviations and formulas have the meanings indicated: Abbreviation Meaning Boc fer-butoxycarbonyl BOP benzotriazole-1-yloxytris (dimethylamino) -phosphonium hexafluorophosphate AcOH acetic acid Comp. compound DBU 1.8-diazabicyclo [5.4.0] undec-7-ene DCM Dichloromethane DIEA? /, / V-diisopropyl ethyl amine DME ethylene glycol dimethyl ether DMF A /, / V-dimethylformamide DMSO dimethyl sulfoxide EtOAc ethyl acetate EtOH Ethanol HPLC liquid chromatography high resolution LiOH lithium hydroxide Min Minute (s) n-Buu n-butyl lithium h / hr / hrs hour (s) mCPBA m-chloroperbenzoic acid MeOH methanol MTBE methyl-t-butylic acid PdCI2 (dppf) or complex [1.1 '-bis- (diphenylphosphino) ferrocene] dichloropalladium Pd (dppf) CI2CH2CI2 (ll) -dichloromethane Pd (PPh3) 4 tetrakistriphenylphosphine palladium TA or at room temperature TBAB tetrabutylammonium bromide TBSOTf f-butyldimethylsilyl trifluoromethanesulfonate Et3N triethylamine TFA trifluoroacetic acid THF tetrahydrofuran TLC thin layer chromatography Reaction scheme AA Scheme AA illustrates a general synthesis of benzimidazoles of formula AA5, representative of a compound of Formula (I).
Typically, a solution of 4-bromobenzene-1,2-diamine AA1 and a suitable carboxylic acid AA2 in phosphorus oxychloride (POCI3) is heated to reflux to obtain bromobenzimidazole AA3. Alternatively, the acid can be converted to an acid chloride using oxalyl chloride and a catalytic amount of DMF in a solvent such as methylene chloride. The acid chloride AA2 is heated with 4-bromobenzene-1,2-diamine AA1 in acetic acid to give AA3. A phenyl group suitably substituted can be attached to AA3 by a variety of coupling reactions (Suzuki, Stille) which are well known to those skilled in the art. A particularly useful substitution method employs a palladium-catalyzed crossed Suzuki coupling reaction (Huff, B. et al, Org Syn 1997, 75: 53-60; and Goodson, FE et al., Syg. 1997, 75: 61-68).
As an example, a mixture of the bromobenzimidazole AA3 is reacted with a suitable phenylboronic acid AA4 in the presence of a reagent such as cesium carbonate and a catalytic amount of palladium catalyst such as PdCI2dppf in a solvent such as a mixture of dioxane and ethanol a elevated temperatures to give AA5. The reaction times can be reduced by the mode of this procedure at similar temperatures (about 100 ° C) or lower temperatures in a microwave synthesizer. Other palladium catalysts suitable for this type of reaction include Pd (PPh3) 4.
Reaction scheme BB The required cinnamic acids can be synthesized by means of the procedures described in reaction scheme BB.
OH A solution of arylaldehyde BB1 and (carbethoxymethylene) triphenyl phosphorane in a solvent such as toluene or benzene in the presence of a base such as NaOH is usually stirred at elevated temperatures to give the corresponding cinnamate ester. The ester is hydrolyzed under standard conditions to provide the corresponding cinnamic acid BB2.
A (R4) r BB2 H ° 2C BB3 The required phenylpropionic acid BB3 can be synthesized from cinnamic acid BB2 by hydrogenation by a variety of standard procedures. As shown above, a mixture of BB2 in ethanol with a catalytic amount of palladium in carbon (10%) is stirred at room temperature under a hydrogen atmosphere [344.5 kPa (50 psi)] to give the acid BB3.
Reaction scheme BB 'The reaction scheme BB' is a variant of the reaction scheme BB.
A (R4) r OHC-A (R4) r CH2 (C02H) 2 ^ H02C BB1 BB2 The reaction of aldehyde BB1 with malonic acid and a catalytic amount of piperidine in pyridine at elevated temperatures produces cinnamic acid BB2 with high yield The BB2 acid is converted to the acid chloride by reaction with oxalyl chloride and a catalytic amount of DMF in a solvent such as methylene chloride. The acid chloride is then heated with AA1 in acetic acid to give?, Which is further processed in place of AA3 as described in reaction scheme AA.
CC Reaction Scheme The CC reaction scheme provides a method for preparing intermediate substituted 4-bromobenzene-1,2-diamines.
CC1 CC2 As an example, to a solution of suitably substituted 4-bromoaniline CC1 in trifluoroacetic anhydride KN03 is added in portions at a suitable temperature. Then the reaction mixture can be heated to room temperature for optimal conversion to nitroamide CC2.
CC3 Sequentially, by standard procedures, the amide is hydrolysed and the nitro group is reduced to give bromodiamine CC3. The intermediate CC3 is further elaborated as described in reaction scheme AA.
DD reaction scheme An alternative synthesis sequence for producing the compounds of the present invention is described in the DD reaction scheme.
A substituted bromobenzimidazole DD1 (representative of AA3 in the AA scheme) is protected (by a protecting group such as Boc), then converted to the pinacolboronate ester DD2 under standard Suzuki coupling conditions (Prieto, M. et. Al., J Org Chem, 2004, 69: 6812-6820, McDonald, D. et al, Bioorg, Med Chem Lett, 2005, 15: 5241-5246, and Poon, SF, Al, Bioorg, Med. Chem. Lett. 2004, 14, 5477-5480). In a typical procedure, a mixture of bromo-benzimidazole DD1, bis- (pinacolato) diboro, potassium carbonate and a catalytic amount of a palladium catalyst such as PdC dppf in DMF is heated at elevated temperatures to give the boronate ester DD2. Frequently, reaction times can be reduced by performing this procedure at similar or lower temperatures in a microwave irradiation apparatus.
The boronate ester DD2 can be converted to the compounds of the present invention (Boc-protected DD3) by coupling Suzuki with a methyl halide, mesylate or triflate. In that case, the borane DD2 is reacted with a suitable aryl halide , tetrakis (triphenylphosphine) palladium (0) and tri-tert-butylphosphonium tetraluoroborate in 2M aqueous potassium carbonate in toluene at 100 ° C to give the protected form of DD3. Deprotection with an acid such as TFA provides DD3.
Reaction Scheme EE Reaction Scheme EE describes methods for preparing representative compounds of the present invention.
The aniline EE1 can be converted to a variety of amides, carbamates or ureas EE2 through the use of any number of acylation methods that are commonly used by those skilled in the art. As an example, the reaction of EE1 in a solvent such as THF with a substituted acid chloride and a base such as triethylamine provides the corresponding amide of EE2. As a further example, the reaction of EE1 in THF with a substituted chloroformate and triethylamine gives the corresponding substituted carbamate of EE2. EE1 can be converted to sulfonamides by the use of various suifonilation conditions. For example, reaction of EE1 in a solvent such as THF with an alkylsulfonyl chloride and triethylamine provides the alkylsulfonamide EE3. The EE1 can be replaced selectively and successively to give EE3. An efficient method of achieving this is by means of a reductive alkylation with aldehydes or ketones (see Mattson, R. J. et al., J. Org. Chem. 1990, 55, 2552-2554) and references mentioned therein]. In this procedure, equal proportions of EE1 and an aldehyde or ketone are stirred with titanium (IV) isopropoxide, followed by the addition of sodium cyanoborohydride in a solvent such as ethanol to provide the substituted amine EE3 FF Reaction Scheme A synthetic sequence for producing compounds of the present invention wherein L is cyclopropyl is described in the FF reaction scheme.
The reaction of the cinnamate ester FF1, in this case a methyl ester, with trimethylsulfonium methylide iodide in a solvent such as DMSO and sodium hydride (as exemplified in Burger, A. et al., J. Med. Chem. 1970, 13, 33-35), provides a cyclopropyl ester FF2. Hydrolysis of FF2 provides the acid FF3, which is further transformed into the benzimidazoles described in the AA scheme.
GG Reaction Scheme The GG reaction scheme describes an alternative method for preparing acid intermediates with cyclopropyl group.
The cinnamic acids are converted to the corresponding Weinreb amide by conversion to the acid chloride as described in Reaction Schemes AA and BB '. The acid chloride is reacted with?,? - dimethylhydroxylamine hydrochloride and a base such as triethylamine in methylene chloride to provide the amide GG2. The amide GG2 is converted to cyclopropyl amide GG3 as described in the FF scheme. The GG3 amide is then hydrolyzed to provide the GG4 acid, typically by reaction with tertiary potassium butoxide in THF.
Reaction Scheme HH A synthesis sequence for producing the compounds of the present invention wherein R-iAr is benzenesulfonamide is described in the reaction scheme HH.
The coupling by the Suzuki reaction of the boronate ester DD2 of the reaction scheme DD and bromobenzene-t-butylsulfonamide HH1 followed by deprotection with TFA gives the product HH2.
Reaction Scheme II A synthetic sequence for producing the compounds of the present invention wherein R is an ether group is described in Reaction Scheme II.
R-OH An ester of commercially available 4-hydroxycinnamic acid 111 can be converted to analogous ethers by several routes including the Williamson reaction. In this well-known procedure 111 and an alkyl halide is reacted with a base such as cesium carbonate in a solvent such as acetonitrile to provide product 112. The most effective electrophiles can be derived from alcohols such as mesylates, p-toluenesulfonates or trifluoromethanesulfonates (triflates). An effective alternative method is the conversion of 111 to analogous ethers II2 by means of the Mitsunobu reaction (reviewed by Mitsunobu, O., Synthesis, 1981, 1-28).
II3 The analogous ethers II2 can be further reduced by acid 113 by standard techniques.
Reaction Scheme JJ Reaction Scheme JJ describes methods for preparing cinnamic acids containing substituted amino groups.
JJ4 The cinnamate ester JJ1 can be converted to a variety of amides, carbamates or ureas JJ2 by utilizing any number of acylation methods that are commonly used by persons skilled in the art. As an example, the reaction of JJ1 in a solvent such as THF with a substituted acid chloride and a base such as triethylamine provides the corresponding amide of J2. As a further example, the reaction of JJ1 in THF with a substituted chloroformate and triethylamine provides the substituted carbamate of JJ2. JJ1 can be converted to sulfonamides by use of various sulfonylation conditions. For example, the reaction of JJ1 in a solvent such as THF with an alkylsulfonyl chloride and triethylamine provides the alkylsulfonamide JJ3. JJ1 can be replaced selectively and successively to provide JJ4. An efficient substitution method is by means of reductive alkylation with aldehydes or ketones (see Mattson, R. J. et al., J. Org. Chem., 1990, 55, 2552-2554 and references mentioned therein). In this process, equal amounts of JJ1 and an aldehyde or ketone are stirred with titanium (IV) isopropoxide, followed by the addition of sodium cyanoborohydride in a solvent such as ethanol to provide the substituted amine JJ4.
KK Reaction Scheme A synthetic sequence for preparing the compounds of the present invention wherein L is acetylene is described in Reaction Scheme KK.
KK1 KK2 When not available on the market, propionic acids KK2 are prepared by reacting acetylenes KK1 with n-butyl lithium in THF at -78 ° C by heating at 0 ° C for 30 min. The mixture is cooled to -78 ° C, and transferred to a saturated solution of carbon dioxide in THF at -78 ° C. The reaction is heated slowly to rt to provide the corresponding propylic acid KK2.
The reaction of propylic acid KK2 with hydrochloride 4-bromobenzene-1,2-diamine KK3 in refluxing ethylene glycol provides chlorovinylbenzimidazole KK4.
The reaction of KK3 with a phenyl boronic acid under Suzuki conditions in a microwave synthesizer and thermal conditions described in Reaction Scheme AA provides acetonic KK4 compounds.
Reaction Scheme LL An alternative synthesis sequence for producing the compounds of the present invention is described in reaction scheme LL.
The protected bromodiamine LL1 is coupled with a suitable boronic acid by means of the Suzuki coupling described in the previous reaction schemes to provide the diamine LL2.
The LL2 is then reacted with an acid or acid chloride to provide LL3 (as described in reaction schemes AA or BB ').
Reaction scheme MM An alternative synthesis sequence for producing the compounds of the present invention where L is vinyl or ethyl which can be used as an alternative to scheme BB 'is described in the MM reaction scheme.
HCI A solution of AA1 and dichloroimine M 1 (as described in McElvain, SM et al., J. Am. Chem. Soc. 1942, 64, 1825) in ethanol is heated to provide the chloromethyl benzimidazole MM2 (as described in US Pat. Komoriya et al., Bioorg, Med. Chem., 2004, 12, 2099-21 14).
Heating in dichloroethane with triphenylphosphine converts M2 into the phosphonium salt M3.
The reaction of MM3 with various aldehydes or ketones in an anhydrous THF solution and EtOH with a base such as DBU (1.8-diazabicyclo [4.5.0] undec-7-ene) provides bromobenzimidazole ??? , which is further elaborated as described in reaction scheme AA.
NN Reaction Scheme An alternative synthesis sequence for producing compounds of the present invention is described in the NN reaction scheme.
The biaryldiamine LL2 is reacted with the dichloroimine MM1 described in the MM reaction scheme to provide NN1.
As described in the MM reaction scheme, NN1 is converted to give NN2.
Reaction scheme 00 The compounds of the present invention wherein L is ethylene can be prepared by the alternative route described in the OO Reaction Scheme.
The compounds of the present invention such as NN3, where L is vinyl, are dissolved in a solvent such as methanol, and are hydrogenated by a catalyst such as 10% Pd in carbon to give 001 PP Reaction Scheme A synthetic sequence for producing compounds of the present invention wherein L is cyclopropyl is described in the PP reaction scheme.
The reaction of the olefin PP1 with an alkyl diazoacetate, such ethyl diazoacetate, in the presence of a catalyst, such as copper trifluoromethane sulphonate (I) and Evans chiral ligand (Evans, DA; Woerpel, K; Hinman, MM Faul, MMJAm, Chem. Soc. 1991, 1 13, 726-728) in a solvent such as chloroform, provides an enantiomer of the cyclopropyl ester PP2. The (R, R) -cyclopropyl ester PP2 enantiomer is obtained when using a chiral ligand such as compound 38b, 2.2-bis- [2 - ((4S) - (1,1-dimethylethyl) -1,3-oxazolinyl)] propane. The (S, S) -cyclopropyl ester enantiomer is obtained when using the chiral ligand, compound 38a, 2,2-bis- [2 - ((4R) - (1,1-dimethylethyl) -1,3-oxazolinyl)] propane. The cyclopropyl residue configurations were predicted on the basis of the Evans J. Am report. Chem. Soc. 1991. The hydrolysis of the ester PP2 gives the acid PP3, which is subsequently transformed into the benzimidazoles of the AA scheme.
PP4 To determine the enantiomeric excess of the asymmetric cyclopropanation products PP2, the PP3 acid is reacted with N, O-dimethylhydroxyl amine in the presence of a base such as diisopropylethylamine, and an amide coupling reagent such as BOP, in a solvent such as DMF to produce methoxy methyl amide PP4. The 1 H NMR resulting from the amide PP 4 in the presence of an appropriate amount of a chiral displacement agent, such as (R) - (-) - 2,2,2-trifluoro-1- (9-anthryl) ethanol, provides the resolution of the baseline of the resulting methoxy singlet. The relationship of the integration of the methoxy singlet gives the value of ee. Thus, NMR showed the methoxy singlet about 3.47 and 3.45 ppm. The integration of the singlet was 1 and 99, respectively; in this way an ee value of 99% is obtained.
QQ Reaction Scheme A synthetic sequence for producing compounds of the present invention wherein F is an alcohol is described in the QQ reaction scheme.
As elaborated in scheme BB ', the aldehyde QQ1 is reacted with malonic acid and a catalytic amount of piperidine in pyridine at elevated temperatures to provide a QQ2 acid. The QQ2 acid is converted to a QQ3 acid chloride by reaction with oxalyl chloride and a catalytic amount of DMF in a solvent such as methylene chloride.
As elaborated in the AA scheme, the QQ3 acid chloride is heated with 4-bromobenzene-1,2-diamine AA1 in acetic acid to give a bromobenzimidazole QQ4.
As elaborated in the AA scheme, an appropriately substituted phenyl boronic acid is reacted with benzimidazole QQ4 in the presence of a reagent and a catalytic amount of a palladium catalyst in a solvent to provide a benzimidazole QQ5 substituted with alcohol, representative of a compound of Formula (I).
EXAMPLE 1 (a-1- (2 2-2 2 - (4-tert-butyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -ethanone (Compound 1) Step A (E) -5-Bromo-2-f2- (4-tert-butyl-phenyl) -vinyl-1 H-benzimidazole To a solution of 3- (4-tert-butyl-phenyl) -acrylic acid (12 g, 58.7 mmoles) in POCI3 (200 mL), 4-bromo-benzene-1,2-diamine (10g, 53.4 mmol) was slowly added. The solution was refluxed for 18 h. The solution was concentrated, and the residual POCI3 was azeotropically removed with toluene. The residue was partitioned between EtOAc and 10% Na 2 CO 3. The organic phase was washed with brine, dried with Na 2 SO 4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, EtOAc: hexanes, 3: 7) to give the title compound 1a (7.1 g, 31% yield). H-NMR (400 MHz, CDCl 3) d (ppm): 7.64 (d, 1 H, J = 13.9 Hz) 7.62 (s, 1 H) 7.41 (d, 2 H, J = 8.4 Hz) 7.36 (d, 1 H , J = 8.5 Hz) 7.33 (d, 2H, J = 8.4 Hz) 7.28 (s, 1 H) 7.22 (dd, 1 H, J = 1.8 Hz, J = 8.5 Hz) 7.02 (d, 1 H, J = 16.5 Hz) 1 .25 (s, 9H).
Step B (a-1- (2- (2-r2- (4-tert-butyl-phenyl) -vinill-1 H-benzimidazol-5-yl) -phenyl) -ethanone A solution of Compound 1a (0.106 g, 0.30 mmol) ), 2-acetylbenzeneboronic acid (136 mg, 0.76 mmole), PdCI2dppf (0.06 mmole) and Cs2CO3 (0.244 g, 0.75 mmole) in 1.4-dioxane: EtOH 5: 1 was heated at 1 15 ° C. After 18 h, The solution was cooled and concentrated.The residue was purified by preparative TLC plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes 3: 7) to give the title compound 1 (0.0146 g). NMR (400 MHz, CD3OD) d (ppm): 7.54 (m, 1 1 H) 7.23 (dd, 1 H, J = 1.6 Hz, J = 8.3 Hz) 7.15 (d, 1 H, J = 16.5 Hz) 2.02 (s, 3H) 1 .36 (s, 9H) MS (ESI, pos. ion) m / z: 395.3 (M + 1) By the procedures described in Example 1 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 3 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenol The title compound (0..048 g) was prepared from 2-hydroxybenzeneboronic acid (0.0345 g), 0.25 mmole) and Compound 1a (0.029 g, 0.1 mmole). H-NMR (400 MHz, CDCl 3) d (ppm): 7.56 (s, 1 H) 7.31 (dd, 2 H, J = 12.2 Hz, J = 24.1 Hz) 7.10 (m, 8H) 6.86 (t, 1 H, J = 7.3 Hz) 6.78 (d, 1 H, J = 16.4 Hz) 1.19 (s, 9H). MS (ESI, pos. Ion) m / z: 368.3 (M + 1). 4 (E) -N- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzyldazol-5-yl.} - phenyl) -acetamide The compound of the title (0.001 g) was prepared from 2-N-acetyl-benzeneboronic acid (0.136 g, 0.76 mmole) and Compound 1a (0.106 g, 0.3 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.44 (m, 4 H) 7.24 (m, 6 H) 6.91 (d, 1 H, J = 12.4 Hz) 6.47 (d, 1 H, J = 12.4 Hz) 1.86 (s, 1 H) 1.20 (s, 9H). MS (ESI, pos. Ion) m / z: 410.2 (M + 1). 5 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} - benzamide The title compound (0.001 g) was prepared from 2-aminocarbonyl-benzeneboronic acid (0.136 g, 0.76 mmole) and Compound 1a (0.106 g, 0.3 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.48 (m, 6 H) 7.37 (m, 5 H) 7.26 (dd, 1 H, J = 1.6 Hz, J = 8.3 Hz) 7.04 (d, 1 H, J = 16.5 Hz) 1.26 (s, 9H). MS (ESI, pos. Ion) m / z: 396.1 (M + 1). 6 (E) -3-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzamide The title compound (0.001 g) was prepared from 3-aminocarbonylbenzene boronic acid (0.136 g, 0.76 mmol) and Compound 1a (0.106 g, 0.3 mmol). H-NMR (400 MHz, CD3OD) d (ppm) 8.22 (t, 1 H, J = 1.7 Hz) 7.88 (m, 3H) 7.62 (m, 6H) 7.51 (m, 2H) 7.17 (d, 1 H, J = 16.5 Hz) 1.38 (s, 9H). MS (ESI, pos. Ion) m / z: 396.1 (M + 1). 7 (E) -4-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} benzamide The title compound (0.002 g) was prepared from 4-aminocarbonylbenzeneboronic acid (0.136 g, 0.76 mmole) and Compound 1a (0.106 g, 0.3 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.97 (m, 2 H) 7.77 (m, 4 H) 7.60 (m, 4 H) 7.47 (d, 2 H, J = 8.4 Hz) 7.13 (d, 1 H, J = 16.5 Hz) 1.36 (s, 9H). MS (ESI, pos. Ion) m / z: 410.2 (M + 1). 8 (£) -N- (4- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide The compound of the title 0.0038 g) was prepared from 4-N-acetylbenzeneboronic acid (0.136 g, 0.76 mmole) and Compound 1a (0.106 g, 0.3 mmole) to provide the title compound (0.0038 g). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.73 (m, 2 H) 7.61 (m, 7 H) 7.49 (m, 3 H) 7.12 (d, 1 H, J = 16.5 Hz) 2.17 (s, 3 H) 1.36 (s, 9H). MS (ESI, pos. Ion) m / z: 410.2 (M + 1).
Comp. Name and data 9 (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl. .phenyl) methanesulfonamide The title compound (0.0045 g) was prepared from the benzene-2-methanesulfonamide (0.163 g, 0.76 mmol) and Compound 1a (0.106 g, 0.3 mmol). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.62 (m, 6 H) 7.50 (d, 2 H, J = 8.5 Hz) 7.41 (m, 2 H) 7.34 (m, 2 H) 7.17 (d, 1 H, J = 16.5 Hz) 2.75 (s, 3H) 1.37 (s, 9H). MS (ESI, pos. Ion) m / z: 446.2 (M + 1). 10-tert-bultyl ester of (£) - (2. {2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -carbamic The title compound (0.0016 g) was prepared from 2-N-Boc-benzeneboronic acid (0.180 g, 0.76 mmol) and Comp. 1b (E) -5- bromo-2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-aminobenzimidazole (0.106 g, 0.3 mmol). 1 H NMR (400 MHz, CD 3 OD) d (ppm) 7.62 (m, 5 H) 7.50 (m, 2 H) 7.33 (dd, 1 H, J = 1.6 Hz, J = 8.3 Hz) 7.14 (m, 3 H) 6.83 ( m, 2H) 3.37 (s, 9H) 1.37 (s, 9H). MS (ESI, pos. Ion) m / z: 468.1 (M + 1). 11 (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} phenylamine A solution of (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl-tert-butyl ester .). phenyl) -carbamic acid (0.005 g, 0.01 mmol) in methylene chloride (1 mL) was treated with trifluoroacetic acid (0.5 mL). The solution was stirred at room temperature for 4 h, then concentrated to give the title compound (0.003 g). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 8.03 (d, 1 H, J = 16.5 Hz) 7.90 (d, 1 H, J = 8.5 Hz) 7.85 (s, 1 H) 7.74 (d, 2H, J = 8.4 Hz) 7.65 (dd, 1 H, J = 1.5 Hz, J = 8.5 Hz) 7.59 (d, 2H, J = 8.4 Hz) 7.43 (m, 5H) 1.39 (s, 9H). MS (ESI, pos. Ion) m / z: 368.1 (M + 1). 12 (/) - (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol The title compound ( 0.0046 g) was prepared from 2-hydroxymethylbenzeneboronic acid (0.102 g, 0.76 mmole) and Compound 1a (0.106 g, 0.3 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.59 (m, 5 H) 7.49 (d, 2 H, J = 8.4 Hz) 7.40 (m, 2 H) 7.34 (m, 2 H) 7.27 (dd, 1 H, J = 1.6 Hz, J = 8.3 Hz) 7.16 (d, 1 H, J = 16.6 Hz) 4.58 (s, 2H) 1.37 (s, 9H). MS (ESI, pos. Ion) m / z: 383.2 (M + 1). 24 (E) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide Via the procedure of Example 1, Step B, the title compound (0.001 g) was prepared from 2-N-acetylbenzeneboronic acid (0.136 g, 0.76 mmole) and Compound 1c (£) -5-bromo-2- [2- (3,4- difluoro-phenyl) -vinyl] -1 H -benzimidazole (0.10 g, 0.30 mmol). 1 H NMR (400 MHz, CD 3 OD) d (ppm) 7.61 (m, 5 H) 7.39 (m, 6 H) 7.18 (d, 1 H, J = 16.5 Hz) 1.99 (s, 3 H). MS (ESI, pos. Ion) m / z: 390.2 (M + 1).
Comp. Name and data 25 (£) -N- (3- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide The compound of the title (0.0102 g) was prepared from the acid "3-N-acetylbencenboronic acid (0.136 g), 0.76 mmole) and Compound 1c (0.10 g, 0.30 mmole). H-NMR (400 MHz, CD3OD) d (ppm) 7.78 (d, 1 H, J = 0.9 Hz) 7.63 (s, 1 H) 7.44 (m, 5H) 7.26 (m, 4H) 7.01 (d, 1 H , J = 16.5 Hz) 2.06 (s, 3H). MS (ESI, pos. Ion) m / z: 390.1 (M + 1). 26 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - benzamide The title compound (0.0031 g) was prepared from 2-aminocarbonylbenzene boronic acid (0.125 g, 0.76 mmol) and Compound 1c (0.10 g, 0.30 mmol). 1 H-NMR (400 MHz, CDCl 3 + CD 3 OD) d (ppm) 7.62 (s, 1 H) 7.40 (m, 9H) 7.18 (td, 1 H, J = 8.4 Hz, J = 10.1 Hz) 7.01 (d, 1 H, J = 16.5 Hz). MS (ESI, pos. Ion) m / z: 376.2 (M + 1). 27 (E) -1- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] - H -benzimidazol-5-yl}. Phenyl) -ethanone The title compound (0.001 g) was prepared from 2-acetylbenzeneboronic acid (0.125 g, 0.76 mmole) and Compound 1c (0.10 g, 0.30 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.49 (m, 5 H) 7.37 (m, 4 H) 7.23 (td, 1 H, J = 8.4 Hz, J = 10.3 Hz) 7.14 (dd, 1 H, J = 1.7 Hz, J = 8.3 Hz) 7.06 (d, 1 H, J = 16.5 Hz) 1.91 (s, 3H). MS (ESI, pos. Ion) m / z: 375.2 (M + 1). 28 (E) -N- (2- { 2- [2- (3,4-difluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide The title compound (0.0021 g) was prepared from 2-methylsulfonylamino benzeneboronic acid (0.163 g, 0.76 mmole) and Compound 1c (0.10 g, 0.30 mmole). H-NMR (400 MHz, CD3OD) d (ppm) 7.50 (m, 5H) 7.36 (m, 1 H) 7.26 (m, 5H) 7.07 (d, 1 H, J = 6.5 Hz) 2.64 (s) , 3H). MS (ESI, pos. Ion) m / z: 426.1 (M + 1). 30 (E) -2- [3- (4-tert-Butyl-phenyl) -propyl] -5-m-tolyl-1 H-benzyldazole The title compound (0.0182 g) was prepared from the 3- methylphenylbenzanboronic acid (0.052 g, 0.38 mmol) and. Compound 5a 5-bromo-2- [3- (4-tert-butyl-phenyl) -propyl] -1H-benzimidazole (0.055 g, 0.15 mmol). 1 H NMR (400 MHz, CDCl 3) d (ppm) 7.33 (m, 3 H) 7.18 (m, 5 H) 7.03 (d, 1 H, J = 7.4 Hz) 6.95 (d, 2 H, J = 8.3 Hz) 2.85 ( m, 2H) 2.57 (t, 2H, J = 7.5 Hz) 2.30 (s, 3H) 2.06 (m, 2H) 1.17 (s, 9H). MS (ESI, pos. Ion) m / z: 383.2 (M + 1).
EXAMPLE 2 (-1- (2- 2-r2- (4-tert-butyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -ethanol (Compound 2) A solution of Comp. 1 (E) -1- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -H-benzimidazol-5-yl.} - phenyl) -ethanone (0.005 g, 0.01 mmol) in ethanol (0.5 ml) was treated with NaBH 4 (0.003 g, 0.08 mmol). After 3 h, the reaction mixture was applied to a preparative TLC plate (2000 microns, silica gel, 20 x 20) and developed by EtOAc: hexanes 1: 1. The desired band was extracted and concentrated to provide the title compound (0.002 g). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.69 (m, 1 H) 7.62 (m, 3 H) 7.50 (m, 3 H) 7.41 (ddd, 2 H, J = 2.5 Hz, J = 10.1 Hz, J = 14.1 Hz) 7.32 (dt, 1 H, J = 1.4 Hz, J = 7.5 Hz) 7.23 (m, 2H) 7.17 (d, 1 H, J = 16.5 Hz) 4.99 (q, 1 H, J = 6.3 Hz) 1.38 (s, 9H) 1.35 (d, 1.5H, J = 6.1 Hz) 1.33 (d, 1.5H, J = 6.1 Hz). MS (ESI, pos. Ion) m / z: 397.2 (M + 1).
EXAMPLE 3 (E) -2 2- [2- (4-trifluoromethyl-phenyl) -vinH ^ (Compound 13) Step A (E) -5-bromo-2-f2- (4-tri † luoromethyl-phenyl) -vinyl-1 H-benzimidazole. By the procedure of Example 1, Step A, the title compound 10c (0.910 g) was prepared at from Compound 10a 3- (4-trifluoromethyl-phenyl) -acrylic acid (1.5 g, 6.9 mmol) and 4-bromo-benzene-1,2-diamine (1.3 g, 6.9 mmol). 1 H NMR (400 MHz, CDCl 3 + DMSO (d 6)) d (ppm) 7.78 (d, 1H, J = 16.5 Hz) 7.73 (d, 1 H, J = 1.7 Hz) 7.66 (m, 4H) 7.48 (d, 2H, J = 8.0 Hz) 7.33 (dd, 1 H, J = 1.8 Hz, J = 8.5 Hz) 7.23 (d, 1 H, J = 16.5 Hz).
Step B (E) -2- (2- [2- (4-trifluoromethyl-phenyl) -vinyl-1H-benzimidazol-5-yl) -benzamide. By the procedure of Example 1, Step B, the title compound (0.001 g) was prepared from 2-carboxamidophenylbenzeneboronic acid (0.120 g, 0.76 mmole) and Compound 10c (0.110 g, 0.30 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.74 (d, 2 H, J = 8.2 Hz) 7.63 (m, 3 H) 7.57 (s, 1 H) 7.40 (m, 6 H) 7.22 (d, 1 H, J = 16.5 Hz). MS (ESI, pos. Ion) m / z: 408.1 (M + 1).
Through the procedures described in Example 3 and the reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention: Comp. Name and data (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenol The title compound (0.001 g) was prepared from 2-hydroxybenzeneboronic acid (0.105 g, 0.38 mmol) and Compound 10c (0.110 g, 0.30 mmol). 1 H-NMR (400 Hz, CD 3 OD) d (ppm) 7.74 (d, 2 H, J = 8.3 Hz) 7.63 (dd, 3 H, J = 8.7 Hz, J = 17.1 Hz) 7.56 (s, 1 H) 7.50 (d , 1 H, J = 8.3 Hz) 7.38 (dd, 1 H, J = 1.5 Hz, J = 8.4 Hz) 7.22 (m, 2H) 7.06 (m, 1 H) 6.82 (m, 2H). MS (ESI, pos. Ion) m / z: 381.3 (M + 1). (E) -1 - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl) -1 H -benzimidazol-5-yl} phenyl) -ethanone The title compound (0.001 g) was prepared from 2-acetylbenzeneboronic acid (0.125 g, 0.76 mmole) and Compound 10c (0.110 g, 0.30 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.75 (d, 2 H, J = 8.2 Hz) 7.60 (m, 4 H) 7.48 (m, 2 H) 7.38 (m, 3 H) 7.23 (d, 1 H, J = 16.6 Hz) 7.16 (dd, 1 H, J = 1.7 Hz, J = 8.3 Hz) 1.92 (s, 3H). MS (ESI, pos. Ion) m / z: 407.3 (M + 1). (E) -1 - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol A solution of Compound 15 ( £) -1- (2- { 2- [2- (4-trifluoromethy1-pheny1) vinyl] -1 H -benzimidazol-5-yl}. Phenyl) -ethanone (0.005 g , 0.01 mmol) in ethanol (0.5 ml) was treated with NaBH, (0.003 g, 0.08 mmol). After 3 h, the solution was applied to a preparative TLC plate (2000 microns, silica gel, 20 x 20) and developed by 1: 1 EtOAc: hexanes. The desired band was extracted and concentrated to provide the title compound (0.001 g). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.87 (d, 1 H, J = 8.2 Hz) 7.76 (d, 1 H, J = 8.0 Hz) 7.67 (m, 1 H) 7.51 (s, 1 H ) 7.42 (m, 1 H) 7.32 (m, 1 H) 7.25 (m, 1 H) 4.98 (q, 1 H, J = 6.4 Hz) 1.35 (d, 1 H, J = 6.4 Hz). MS (ESI, pos. Ion) m / z: 409.2 (M + 1).
Comp. Name and data 17 (£) -N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide The compound of the title (0.094 g) was prepared from 2-methylsulfonyl aminobencenboronic acid (0.163 g), 0.76 mmole) and Compound 10c (0.110 g, 0.30 mmole). H-NMR (400 MHz, DMSO (d6)) d (ppm) 12.82 (s, 1 H) 8.89 (s, 1 H) 7.91 (d, 2H, J = 8.1 Hz) 7.80 (m, 2H) 7.75 (s) , 1H) 7.70 (m, 1H) 7.58 (d, 1 H, J = 6.9 Hz) 7.37 (m, 6H) 2.73 (d, 3H, J = 28.8Hz). MS (ESI, pos. Ion) m / z: 458.2 (M + 1). N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl}. Phenyl) -methanesulfonamide By the procedure of Example 1, Step A , Compound 3b 5-bromo-2- [2- (4-trifluoroethyl-phenyl) -ethyl] -1H-benzimidazole was prepared from 3- (4-trifluoromethyl-phenyl) -propionic acid (1.04 g, 5.04 mmoles) and 4-bromo-benzene-1,2-diamine (0.946 g, 5.06 mmol). By the procedure of Example 1, Step B., the title compound was prepared from 2-methylsulfonylaminobenzeneboronic acid (0.367 g, 1.7 mmole) and Compound 3b (0.188 g, 0.51 mmole). 1 H-NMR (400 MHz, (CD 3 OD) d (ppm) 7.64-7.50 (m, 5H), 7.47-7.34 (m, 4H), 7.34-7.27 (m, 2H), 3.27 (s, 4H), 2.71 ( s, 3H) MS (ESI, pos. ion) m / z: 460.16 (M + 1).
EXAMPLE 4 (E) -2- 2- [2- (4-trifluoromethoxy-phenyl) -vinin (Compound 19) Step A 3- (4-trifluoromethoxy-phenyl) -acrylic acid A solution of 4-trifluoromethoxybenzaldehyde (26.3 mmol), malonic acid (5.6 g, 53.8 mmol) and piperidine (0.265 ml, 2.7 mmol) in pyridine (15 ml) was heated at 70 ° C for 18 h. Water (200 ml) was added to the reaction solution. The mixture was acidified to pH 4 by hydrochloric acid concentrated. The solution was filtered. The solid was washed with water. The solid was dried in vacuo to give the title compound 4a (1.2 g). 1 H-NMR (d 6 -DMSO) d (ppm): 6.80 (d, J = 16.02 Hz, 1 H), 6.72 (m, 2 H), 6.38 (m, 2 H), 5.55 (d, J = 16.00 Hz, 1 H).
Step B 3- (4-trifluoromethoxy-phenyl) -acyloyl chloride A solution of Compound 4a (1.2 g, 5.2 mmol) in methylene chloride (20 mL) was treated with oxalyl chloride (7.8 mL, 3.6 mmol). DMF (0.02 ml) was added to the solution. The reaction solution was stirred at room temperature for 2 h. The reaction solution was concentrated. The residue was dried in vacuo to provide Compound 4b, which was used without further purification in the next step.
Step C (E) -5-Bromo-2- [2- (4-trifluoromethoxy-phenyl) -vinyl-1-H-benzimidazole A solution of Compound 4b (1 g, 4 mmol) in acetic acid (10 mL) was slowly added to a 4-bromo-benzene-1,2-diamine solution (0.744 g, 4 mmol) in acetic acid (10 ml). The solution was heated at 100 ° C for 18 h. The solution was cooled to room temperature. To the solution was added ethyl acetate: hexanes 3: 7 (100 ml). The solution was filtered. The solid was dried in vacuo to give the title compound 4c (1.1 g). 1 H-NMR (400 MHz, DMSO d 6) ppm 8.12 (d, J = 16.60 Hz, 1 H), 7.98 (m, 1 H), 7.87 (m, 2 H), 7.82-7.68 (m, 1 H), 7.67. -7.37 (m, 4H), 7.34 (d, J = 16.58 Hz, 1 H). MS (ESI pos. Ion) m / z: 383.2 and 385.2.
Step D (-2- (2-r2- (4-trifluoromethoxy-phenyl) -vinyl-1 H-benzimidazol-5-yl) -benzamide. By the procedure of Example 1, Step B, the title compound 19 was prepared from 2-carboxamido-phenylbenzeneboronic acid and Compound 4c By the procedures described in Example 4 and reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 20 (E) -1 - (2- { 2- [2- (4-trifluoromethoxy-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} -phenyl ) -etanone The title compound (0.001 g) was prepared from the 2-acetylbenzeneboronic acid (0.280 g, 1.7 mmole) and Compound 4c (0.195 g, 0.51 mmole). 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.66 (d, J = 8.72 Hz, 2H), 7.61-7.43 (m, 4H), 7.43-7.32 (m, 3H), 7.24 (d, J = 8.19 Hz, 2H), 7.19-7.06 (m, 2H), 1.96-1.86 (m, 3H). MS (ESI, Ion pos.) M / z 423.14 (M +). 21 (E) -1 - (2- {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanol By the process of Example 2, the title compound was prepared from Compound 20. 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.76-7.80 (d, J = 8.84Hz, 2H) 7.60-7.70 (m, 3H) 7.50 (bs, 1 H) 7.40-7.44 (ddd, J = 1.26, 7.32Hz, 1 H) 7.29-7.37 (m, 3H) 7.20-7.25 (m, 3H) 4.96-5.02 (q, J = 6.57Hz , 1 H) 1 .34-1 .36 (d, J = 6.32Hz, 3H). MS (ESI, pos. Ion) m / z: 425.2 (M + 1). 22 (E) -N- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -methanesulfonamide The title compound ( 0.05 g) was prepared from 2-methylsulfonyl aminobenzeneboronic acid (0.521 g, 2.4 mmol) and Compound 4c (0.463 g, 1.2 mmol). 1 H-NMR (400 MHz, DMSO (d 6)) d (ppm) 12.76 (d, J = 5.43 Hz, 1 H), 8.90 (d, J = 4.68 Hz, 1 H), 7.83 (d, J = 8.72 Hz , 2H), 7.65 (m, 1 H), 7.50-7.22 (m, 8H), 2.76 (s, 1.5H), 2.69 (s, 1.5H). MS (ESI, pos. Ion) m / z: 474.2 (M + 1).
EXAMPLE 5 2- (2-R3- (4-tert-butyl-phen1) -propin-1H-benzimidazol-5-yl) -phenol (Compound 29) Step A A5-bromo-2- [3- (4-tert-butyl-phenyl) -propyl-H-benzimidazole By the procedure of Example 1, Step A, the compound of title 5a (0.512 g) was prepared from 4- (4-tert-butyl-phenyl) -butyric acid (2.0 g, 10.7 mmol) and 4-bromo-benzene-1,2-diamine (2.0 g, 10.7 mmol). 1 H-NMR (400 MHz, CDCl 3) d (η t) 7.73 (d, 1 H, J = 1.6 Hz) 7.45 (d, 1 H, J = 8.5 Hz) 7.38 (dd, 1 H, J = 1.8Hz, J = 8.5Hz) 7.32 (m, 3H) 7.12 (d, 2H, J = 8.3 Hz) 2.97 (m, 2H) 2.73 (t, 2H, J = 7.4 Hz) 2.23 (m, 2H) 1.33 ( s, 9H).
Step B 2- (2-f3- (4-tert-butyl-phenyl) -propyl-1-H-benzimidazol-5-yl) -phenol By the procedure outlined in Example 1, Step B, the title compound 29 (0.0083 g ) was prepared from 2-hydroxybenzeneboronic acid (0.07 g, 0.5 mmole) and Compound 5a (0.074 g, 0.2 mmole). H-NMR (400 MHz, CDCl 3) d (ppm) 7.51 (s, 1 H) 7.39 (d, 1 H, J = 8.1 Hz) 7.16 (m, 6H) 6.95 (d, 3H, J = 8.2 Hz) 6.88 (t, 1 H, J = 7.4 Hz) 2.73 (t, 2H, J = 7.5 Hz) 2.52 (t, 2H, J = 7.3 Hz) 2.00 (m, 2H) 1.20 (s, 9H). MS (ESI, pos. Ion) m / z: 385.3 (M + 1).
EXAMPLE 6 2- (2-r 2 - (4-tert-butyl-phenyl) -etin-1 H-benzimidazol-5-yl) -phenol (Compound 32) Step A 3- (4-tert-Butyl-phenyl) -propionic acid A mixture of 3- (4-tert-butyl-phenyl) -acrylic acid (12.28 g, 60.1 mmol) and 10% palladium on carbon (0.6 g) in Ethanol was hydrogenated at 344.5 kPa (50 psi) of hydrogen for 2 hours. The reaction mixture was filtered through a pad of celite, a nylon disk and the solvents were removed in vacuo to yield the title compound 6a (12.36 g, 59.9 mmol) as a white crystalline powder. H-NMR (d6-DMSO) d (ppm): 12.10 (s, 1 H), 7.29 (d, 2H), 7.12 (d, 2H), 2.88 (t, 2H), 2.50 (t, 2H), 1.25 (s, 9H). MS (ESI pos. Ion) m / z: 228.9 (M + Na +) Step B 5-Bromo-2- [2- (4-tert-butyl-phenyl) -ethyl-1-H-benzimidazole To a solution of Compound 6a (1.04 g, 5.04 mmol), in 25 mL of POCI3 was added 4-bromo- benzene-1,2-diamine (0.946 g, 5.06 mmol). The reaction mixture was refluxed under a nitrogen atmosphere for 2.5 h then concentrated in vacuo. The residue was treated with 25 ml of benzene and evaporated in vacuo. The residue was partitioned between 50 ml of EtOAc and 50 ml of saturated NaHCO 3. The organic fractions were washed with 50 ml of saturated NaHCO3 and 50 ml of brine. The organic fraction was dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, EtOAc: Heptane 2: 8-4: 6)) to yield the title compound 6b (0.726 g, 2.03 mmol) as a powder. 1 H-NMR (d 6 -DMSO) d (ppm): 12.48-12.32 (m, 1 H), 7.74-7.58 (m, 1 H), 7.51-7.38 (m, 1 H), 7.33-7.22 (m, 3H ), 7.17 (d, 2H), 3.10 (m, 4H), 1.27 (s, 9H). MS (ESI pos. Ion) m / z: 357.1 / 359.1 (M + H +).
Step C 2- (2- [2- (4-tert-butyl-phenyl) -etin-1 H-benzimidazol-5-yl) -phenol A mixture of Compound 6b, (0.036 g, 0.10 mmol), 2-hydroxy phenyl acid boronic (0.022 g, 0.16 mmole), Cs2CO3 (0.074 g, 0.23 mmole) and PdCI2 (dppf) (0.008 g, 0.01 mmole) in 2 ml dioxane / EtOH 5: 1 in a sealed tube was heated at 100 ° C during 15 minutes on a microwave synthesizer. More 2-hydroxy phenyl boronic acid (0.024 g, 0.17 mmol) and more PdCI2 (dppf) (0.010 g, 0.01 mmol) were added and the reaction was heated at 120 ° C for 20 minutes. The reaction mixture was partitioned between 20 mL of EtOAc, 20 mL of water and 2 mL of brine. The organic fraction was evaporated and the residue was purified by chromatography (reversed phase, acetonitrile: water + 0.1% TFA, 25: 75-95: 5). The relevant fractions were frozen and lyophilized to provide the product of Compound 32 (0.03 g, 0.04 mmol) as a tan powder. 1 H-NMR (d 6 -DMSO) d (ppm): 14.55 (br s, 1 H), 9.69 (s, 1 H), 7. 87 (s, 1 H), 7.77 (d, 1 H), 7.65 (d, 1 H), 7.36-7.30 (m, 3 H), 7.24-7.15 (m, 3 H), 6.98 (d, 1 H), 6.92 (t, 1 H), 3.40 (t, 2H), 3.17 (t, 2H), 1.25 (s, 9H). MS (ESI pos. Ion) m / z: 371.2 (M + H +).
Through the procedures described in Example 6 and reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention: Comp. Name and data 33 3-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenol The title compound (0.016 g) was prepared from 3-hydroxyphenyl boronic acid (0.037 g) and Compound 6b (0.036 g). 1 H-NMR (d 6 -DMSO) d (ppm): 14.62 (br s, 1 H), 9.62 (s, 1 H), 7.88 (s, 1 H), 7.81 (d, 1 H), 7.71 (dd, 1 H), 7.36-7.27 (m, 3H), 7.18 (d, 2H), 7.13 (d, 1 H), 7.08 (t, 1 H), 6.82 (dd, 1 H), 3.40 (t, 2H), 3.16 (t, 2H), 1.25 (s, 9H). MS (ESI pos. Ion): 371.2 (M + H +). 34 4-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenol The title compound (0.022 g) was prepared from 4-hydroxyphenyl boronic acid (0.032 g) and Compound 6b (0.036 g). H-NMR (d6-D SO) d (ppm): 14.61 (br s, 1 H), 9.65 (s, 1 H), 7.85 (s, 1 H), 7.78 (d, 1 H), 7.71 (dd) , 1 H), 7.56 (d, 2H), 7.33 (d, 2H), 7.18 (d, 2H), 6.89 (d, 2H), 3.39 (t, 2H), 3.16 (t, 2H), 1.25 (s) , 9H). MS (ESI pos. Ion) m / z: 371.2 (M + H +).
EXAMPLE 7 (E) - (2- ~ f2-r2- (4-trifluoromethylsulfanyl-phenyl) -vinin-1H-benzimidazole-5-ylV phenyl-methanol (Compound 35) Step A Ethyl ester of (E) -3- (4-trifluoromethylsulfanyl-phenyl) -acyclic acid To a solution of 4-trifluoromethylsulfanyl-benzaldehyde (15.46 g, 75.0 mmol) in 350 ml of benzene was added (carbethoxymethylene) triphenyl-phosphorane (26.14 g, 75.0 mmol). The reaction mixture was refluxed under a nitrogen atmosphere for 6 hours. The solvents were removed in vacuo and the resulting material was triturated with 350 ml of diethyl ether and filtered. The filtrate was concentrated in vacuo and triturated once more with 50 ml of diethyl ether. The filtrate was evaporated in vacuo and purified by chromatography (silica, EtOAc: heptane 0: 10-1: 9) to obtain the title compound 7a (15.8 g, 57.3 mmol) as a white solid. 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 7.89 (d, 2 H), 7.75 (d, 2 H), 7.70 (d, 1 H), 6.77 (d, 1 H), 4.21 (q, 2 H) ), 1.27 (t, 3H). MS (ESI pos. Ion) m / z: 217. Q (M + H +).
Step B (E) -3- (4-Trifluoromethylsulfanyl-phenyl) -acrylic acid To a solution of Compound 7a (10.31 g, 37.3 mmol), 3N aqueous NaOH solution (13.0 mL, 39.0 mmol) was added to 300 mL of ethanol. The reaction mixture was stirred for 21 hours, then evaporated in vacuo. The residue was dissolved in 250 ml of water and 1 N aqueous HCl (45 ml, 45 mmol) was added thereto. The resulting precipitate was filtered, rinsed with water and dried under a stream of air to yield the title compound 7b (8.967 g, 36.1 mmol) as a white powder. 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 12.58 (s, 1 H), 7.85 (d, 2 H), 7.74 (d, 2 H), 7.63 (d, 1 H), 6.66 (d, 1 HOUR).
Step C (£ -5-bromo-2-r2- (4-trifluoromethylsulfanyl-phenyl) -vinyl-1-H-benzimidazole To a suspension of Compound 7b (1240 g, 5.00 mmol) in 100 mL of CH3CN was added POCI3 (2.3 mL, 25.1 mmoles) and 4-bromo-benzene-1,2-diamine (0.938 g, 5.01 mmol) The reaction mixture was heated to reflux in a nitrogen atmosphere for 18 hours, cooled slightly and then 4-bromobenzene was added. -1.2-Additional diamine (0.468 g, 2.50 mmol) The reflux continued for 6 hours, then a final amount of 4-bromo-benzene-1,2-diammine (0.468 g, 2.50 mmol) was added. An additional 15 hours, the reaction mixture was concentrated in vacuo, the residue was purified by chromatography (silica, NH3 in MeOH (2M): CH2Cl2, 1: 99-5: 95) then a second time (EtOAc: heptane 1: 9). -1: 1)) to provide the title compound 7c (1.255 g, 3.14 mmol) as a tan powder. 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 12.96-12.83 (br d, 1 H), 7.87-7.68 (m, 6H), 7.60-7.45 (m, 1 H), 7.39-7.29 (m , 2H). MS (ESI pos. Ion) m / z: 398.9 / 400.9 (M + H +).
Step D (a-2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinin-1 H-benzimidazol-5-yl) -phenyl) -methanol To a solution of Compound 7c (0.040 g, 0.10 mmol) and 2-hydroxymethyl phenyl boronic acid (0.029 g, 0. 9 mmoles) in 3 ml of dioxane in a small pressure tube was added a solution of aqueous Na 2 CO 3 (0.13 ml, 2 M, 0.26 mmol) followed by PdCl 2 (dppf) ( 0.008 g, 0.01 mmol). The vessel was injected with argon, capped and heated in an oil bath at 120 ° C for 1 hour. The reaction mixture was partitioned between 20 mL of EtOAc, 20 mL of water and 2 mL of brine. The organic fractions were dried with Na 2 SO 4, filtered and the filtrate was evaporated. The residue was purified by chromatography (reversed phase, acetonitrile: water + 0.1% TFA, 1: 3-95: 5). The relevant fractions were mixed with poly (vinylpyridine), filtered, frozen and lyophilized to give the title compound 35 (0.027 g, 0.063 mmol) as a yellow powder. 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 7.89-7.78 (m, 5H), 7.71-7.57 (m, 3H), 7.44-7.28 (m, 5H), 4.44 (s, 2H). MS (ESI pos. Ion) m / z: 426.7 (M + H +). By the procedures described in Example 7 and reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 36 (E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -H-benzimidazol-5-yl} -phenol The title compound (0.029 g) was prepared from 2-hydroxyphenyl boronic acid (0.028 g) and Compound 7c (0.040 g). 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 9.61 (s, 1 H), 7.90-7.79 (m, 6H), 7.70 (d, 1 H), 7.54 (d, 1 H), 7.42 ( d, 1 H), 7.33 (dd, 1 H), 7.19 (dt, 1 H), 6.98 (d, 1 H), 6.91 (dt, 1 H). MS (ESI pos. Ion) m / z: 412.8 (M + H +). 37 (E) -N- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl] -acetamide The compound of title (0.016 g) was prepared from N- [2- (4.4.5.5-tetramethyl- [1.3.2] d-oxaborolan-2-yl) -phenyl] -acetamide acid (0.052 g) and Compound 7c ( 0.040 g). H-NMR (400MHz, d6-DMSO) d (ppm): 9.24 (s, 1 H), 7.86 (d, 2H), 7.82-7.75 (m, 3H), 7.67 (d, 1 H), 7.57 (s) , 1 H), 7.51 (d, 1 H), 7.44- 7.24 (m, 5H), 1.89 (s, 3H). MS (ESI pos. Ion) m / z: 453.8 (M + H +). 38 (E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzamide The title compound (0.031 g) was prepared from 2-benzamido boronic acid (0.034 g) and Compound 7c (0.040 g). 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 7.91-7.79 (m, 5H), 7.73- 7.66 (m, 3H), 7.54-7.38 (m, 6H), 7.31 (s, 1 H) . MS (ESI pos. Ion) m / z. 439.8 (M + H +). 39 (E) -1- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. Phenyl) -ethanone The title compound ( 0.027 g) was prepared from 2-acetyl phenyl boronic acid (0.034 g) and Compound 7c (0.040 g). 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 7.87 (d, 2H), 7.84-7.77 (m, 3H), 7.69 (d, 1 H), 7.55-7.47 (m, 2H), 7.64- 7.58 (m, 3H), 7.40 (d, 1 H), 7.21 (dd, 1 H), 2.09 (s, 3H). MS (ESI pos. Ion) m / z: 438.7 (M + H +).
EXAMPLE 8 (E) -1- (2 ^ 2 2- (4-Trifluoromethanesulfonyl-phenM) -vinin-1 H-benzimidazol-5-yl-phenyl-ethanone (Comp.40) Step A Acid (E -3- (4-trifluoromethanesulfonyl-phenyl) -acrylic acid To a suspension of Compound 7b (2483 g, 10.01 mmol), in 50 mL of TFA was added 30% H202 solution (8 mL, 83 mmol). The reaction mixture was stirred for 21 h, then poured into 250 ml of ice water.The resulting precipitate was filtered, rinsed with water and dried under vacuum at 50 ° C to yield the title compound 8a (2281 g, 8.14 g. mmoles) as a white powder: 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 12.80 (s, 1 H), 8.15 (s, 4H), 7.73 (d, 1 H), 6.83 (d, 1 H) MS (ESI pos. Ion) m / z: 278.9 (M-H +).
Step B (E) -5-Bromo-2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl-1-H-benzimidazole To a suspension of Compound 8a (1,405 g, 5.01 mmol) in 100 mL of acetonitrile was added POCI 3 (2.3 me, 25.1 mmoles). The reaction mixture was refluxed under a nitrogen atmosphere for 30 minutes, then cooled slowly. To this reaction mixture was added 4-bromo-benzene-1,2-diamine (0.946 g, 5.06 mmol) and the reaction was refluxed for 2 h before adding additional 4-bromo-benzene-1,2-diamine (0.942 g, 5.04 mmol) ). After one hour of heating, the reaction mixture was cooled and filtered through a pad of celite. The filter cake was rinsed with acetonitrile, ethyl acetate and methanol. The filtrate was stirred with aqueous NaHCO3 / EtOAc. The organic fraction was evaporated and partitioned between 100 ml of EtOAc and 100 ml of saturated NaHCO 3. The organic fraction was dried with Na 2 SO 4, filtered and the filtrate was evaporated. The residue was purified by chromatography (silica gel EtOAc: heptane 1: 4-1: 1) to yield the title compound 8b (1595 g, 3.70 mmol) as a tan powder. H-NMR (400 MHz, d6-DMSO) d (ppm): 13.00 (d, 1 H), 8.14 (q, 4H), 7.87-7.73 (m, 2H), 7.63-7.50 (m, 2H), 7.40 -7.33 (m, 1 H). MS (ESI pos. Ion) m / z: 430.8 / 432.8 (M + H +).
Step C (a-1- (2- (2-f2- (4-trifluoromethanesulfonyl-pheny] -vinyl-H-benzimidazol-5-yl) -phenyl) -ethanone A solution of Compound 8b (0.043 g, 0.10 mmol) and 2-acetyl phenyl boronic acid (0.035 g, 0.21 mmol) in 3 ml of dioxane was stirred in a small pressure tube Na2CO3 aqueous solution (0.13 ml, 2M, 0.26 mmol) was added followed by PdCI2 (dppf) (0.007 g, 0.01 mmol). The vessel was cleaned with argon, capped and heated in an oil bath at 120 ° C for 1 h. The reaction mixture was partitioned between 20 mL of EtOAc, 20 mL of water and 2 mL of brine. The organic fraction was dried with Na 2 SO 4, filtered and the filtrate was evaporated. The residue was dropped onto a bag of silica gel with 100% EtOAc and then evaporated. The crude material was purified by chromatography (reversed phase, acetonitrile / water + 0.1% TFA, 1: 3-95: 5). The appropriate fractions were mixed with poly (vinylpyridine), filtered, frozen and lyophilized to give the title compound 40 (0.022 g, 0.047 mmol) as a yellow powder. 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 8.16 (q, 4H), 7.87 (d, H), 7.70 (d, 1 H), 7.64-7.56 (m, 3H), 7.55-7.47 (m, 3H), 7.21 (d, 1 H), 2.09 (s, 3H). MS (ESI on pos.): 471.0 (M + H +). By the procedures described in Example 8 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 41 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vin] -1-H-benzimidazol-5-yl} -phenol The title compound (0.024 g) was prepared from 2-hydroxyphenyl boronic acid (0.029 g) and Compound 8b (0.043 g). H-NMR (400MHz, d6-DMSO) d (ppm): 9.53 (s, 1 H), 8.16 (q, 4H), 7.85 (d, 1 H), 7.77 (s, 1 H), 7.65 (d, 1 H), 7.58 (d, 1 H), 7.47 (d, 1 H), 7.33 (d, 1 H), 7.17 (dt, 1 H), 6.97 (d, 1 H), 6.90 (dt, 1 H ). MS (ESI pos. Ion) m / z 445.0 (M + H +). 42 (£) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenol) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol The compound of title (0.030 g) was prepared from 2-hydroxymethyl phenyl boronic acid (0.027 g) and Compound 8b (0.043 g). 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 8.16 (q, 4H), 7.89 (d, 1 H), 7.69 (d, 1 H), 7.62 (d, 2H), 7.58 (d, 1 H), 7.43-7.33 (m, 2H), 7.30 (dd, 2H), 4.44 (s, 2H). MS (ESI pos. Ion) m / z: 459.0 (M + H +). 43 (£) -N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -H-benzimidazol-5-yl}. Phenyl) -acetamide The title compound (0.01) 1 g) was prepared from N- [2- (4.4.5.5-tetramethyl- [1.3.2] dioxaborolan-2-yl) -phenyl] -acetamide acid (0.053 g) and Compound 8b (0.043 g). H-NMR (400MHz, d6-DMSO) 8 (ppm): 9.23 (s, 1 H), 8.15 (q, 4H), 7.85 (d, 1 H), 7.67 (d, 1 H), 7.62-7.55 ( m, 2H), 7.51 (d, 1 H), 7.42-7.23 (m, 4H), 1.89 (s, 3H). MS (ESI pos. Ion) m / z 486.1 (M + H +). 44 (£) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide The title compound (0.018 g) was prepared from 2-benzamido boronic acid (0.034 g) and Compound 8b (0.043 g). 1 H-NMR (400MHz, d 6 -DMSO) d (ppm): 8.16 (q, 4H), 7.88 (d, 1 H), 7.70-7.64 (m, 3H), 7.59 (d, 1 H), 7.54-7.39 (m, 4H), 7.36 (dd, 1 H), 7.30 (s, 1 H). MS (ESI pos. Ion) m / z: 472.0 (M + H +).
EXAMPLE 9 (E) -1- (2- 2 -R2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl-phenyl) -ethanol (Compound 45) 1- (2- (2-f2- (4-trifluoromethanesulfonyl-phenyl) -etin-1 H-benzimidazole-5-IMeniD-ethanol (Compound 46) To a solution of Compound 40 (0.047 g, 0.10 mmol) in 5 mL of EtOH was added NaBH 4 (0.028 g, 0.74 mmol) After 1 h, an additional amount of NaBH 4 (0.024 g, 0.63 mmol) was added.After an additional 4.5 h, the reaction was diluted in 25 mL of EtOAc and washed twice with 25 ml of water / brine, the organic fractions were dried with Na 2 SO 4, filtered and the filtrate was evaporated, the residue was purified by chromatography (reversed phase (acetonitrile / water with 0.1% TFA, 1: 3). -95: 5) The two products were isolated, frozen and lyophilized to provide the products of Compound 45 (0.024 g, 0.051 mmol) as a yellow powder and Compound 46 (0.020 g, 0.042 mmol) as a white powder. 45: 1H-NMR (400MHz, d6-DMSO) d (ppm): 8.18 (dd, 4H), 7.93 (d, 1 H), 7.74 (d, 1 H), 7.67 (d, 1 H), 7.64- 7.57 (m, 2H), 7.43 (dt, 1 H), 7.35-7.27 (m, 2H), 7.21 (dd, 1 H) , 4.80 (q, 1 H), 1.22 (d, 3H). MS (ESI pos. Ion) m / z: 472.8 (M + H +). Compound 46: 1 H-NMR (400 MHz, d 6 -DMSO) d (ppm): 8.12 (d, 2H), 7.82-7.74 (m, 3H), 7.70-7.63 (m, 2H), 7.47-7.37 (m, 2H), 7.32 (dt, 1 H), 7.18 (dd, 1 H), 4.72 (q, 1 H), 3.47 (t, 2H), 3.40 (t, 2H), 1.19 (d, 3H).
MS (ESI pos. Ion) m / z: 474.8 (M + H +).
EXAMPLE 10 (E) -2- (2- 2-r2- (4-trifluoromethyl-phenyl) -vinn-1 H-benzimidazol-5-yl) -phenyl) - Step A 3- (4-trifluoromethyl-phenyl) -acrylic acid A solution of 4-trifluoromethylbenzaldehyde (7.7 ml, 57.7 mmol), malonic acid (12.0 g, 1 15.4 mmol), 0.567 μ? of piperidine (5.75 mmoles) in 30 ml of pyridine was stirred at 70 ° C for 18 h. The reaction solution was cooled to room temperature. Water (300 mL) was added and the resulting mixture acidified to pH 4 (litmus) using concentrated hydrochloric acid to provide a precipitate. The solid was filtered and washed with water until the filtrate was neutral. The solid product was dried in vacuo to provide the title compound 10a as a white powder (11.2 g, 90%). HRMN (400MHz, DMSO-d6) d (ppm): 12.60 (bs, 1 H), 7.92 (d, 2H, J = 8.2 Hz), 7.77 (d, 2H, J = 8.2 Hz), 7.66 (d, 1 H, J = 16.0 Hz), 6.70 (d, 1 H, J = 16.0 Hz).
Step B (E) -5-Bromo-2- [2- (4-trifluoromethyl-phenyl) -vinyl-1 H-benzimidazole A solution of Compound 10a (20.6 g, 95.4 mmol) in anhydrous methylene chloride (200 ml) was treated with oxalyl chloride (16.6 ml, 190 mmol) and "3 drops" of anhydrous dimethylformamide. The resulting solution was stirred at room temperature in an argon atmosphere for 18 h. The solvent was concentrated to give Compound 10b 3- (4-trifluoromethyl-phenyl) -acyloyl chloride as a solid, which was used without further purification in the next step. To a solution of 4-bromo-benzene-1,2-diamine (16.1 g, 86.7 mmole) in acetic acid (100 ml) was added dropwise a solution of Compound 10b (so-called 95.4 mmole) in acetic acid (100 ml). The reaction mixture was stirred at 100 ° C for 18 h. The reaction mixture was cooled to room temperature, and a mixture of ethyl acetate and hexanes 3: 7 (500 ml) was added. The mixture was triturated at room temperature for 3 h to provide a precipitate. The solid was filtered and dried in vacuo to provide the title compound 10c (23.2 g, 73%). H NMR (400MHz, DMSO-d6 / CDCl 3) d (ppm): 8.45 (d, 1 H, J = 16.7 Hz), 7.84-7.90 (m, 1 H), 7.74 (d, 2H, J = 8.3 Hz) , 7.56-7.62 (m, 3H), 7.50-7.52 (m, 1 H), 7.34 (d, 1 H, 16.7 Hz).
Step C 2- (2-bromo-phenyl) -propan-2-ol To a solution of methyl 2-bromobenzoate (20.76 g, 96 mmol) in 120 ml of anhydrous ether under argon at 0 ° C was slowly added methylmagnesium bromide ( 77 mi, 3.26 M) at a speed such that the internal temperature of the mixture was below 20 ° C. A white suspension was produced and the mixture was stirred at room temperature for 2 h. The mixture was cooled in an ice bath with water. Hydrochloric acid (400 ml, 0.5 M) was added very slowly to the reaction mixture. The pH of the final mixture was adjusted to less than about 6 with a few drops of 2M hydrochloric acid. The layers were separated and the aqueous phase was extracted with ether. The organic phases were combined and dried with magnesium sulfate. The organic fractions were filtered and the filtrate was concentrated to yield the title compound as a pale yellow liquid, which was distilled in vacuo to provide the title compound 10d as a colorless liquid (16.9 g, 82%, p.b. 65-70 ° C / 0.3 mmHg). 1 H NMR (400 MHz, CDCl 3) d (ppm): 7.67 (dd, 1 H, J = 1.7, 7.9 Hz), 7.58 (dd, 1 H, J = 1.3, 7.9 Hz), 7.30 (ddd, 1 H, J = 1.4, 7.4, 7.9 Hz), 7.10 (ddd, 1H, J = 1.7, 7.4, 7.8 Hz), 2.77 (br s, 1H), 1.76 (s, 6H).
Step D 3. 3-dimethyl-3H-benzorcin. 2-oxazole-1-ol To a solution of n-Buu (166 mL, 2.6 M, 432 mmol) in 200 mL of THF at -78 ° C under argon was slowly added a solution of Compound 10d (42.2 g, 196 mmoles) in 60 ml of THF) at such a rate that the internal temperature of the mixture remained below -70 ° C. The mixture was stirred at -75 ° C for 2 h. To the reaction mixture was then added triisopropylborate (59 ml, 255 mmol) in three portions. The mixture was allowed to warm slowly to room temperature overnight. The mixture was then cooled to 0 ° C and carefully quenched with dilute hydrochloric acid (250 ml, 2N). Then the mixture was stirred at room temperature for 1 h. The pH of the mixture was examined and adjusted to acid by additional 2N HCl if necessary. The two layers were separated and the aqueous phase was extracted twice with ether. The organic phases were combined and dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to produce a pale yellow oil. The residue was then diluted with ethyl acetate (400 ml) and washed with a 1 N sodium hydroxide solution (150 ml x 3). The basic aqueous phases were combined and acidified with 2N HCl. The limpid solution turned turbid and acid was added. The mixture was extracted with ether (150 ml x 3). The organic phases were combined and dried with magnesium sulfate. The solution was filtered and the filtrate was concentrated under reduced pressure to yield the title compound 10e as a colorless oil (26.2 g, 82%) which was used without further purification in the next step. 1 H NMR (400MHz, DMSO-d 6) d (ppm): 9.00 (s, 1H), 7.66 (dm, 1 H, J = 7.3 Hz), 7.45 (dt, 1 H, J = 1.1, 7.7 Hz), 7.40 (dm, 1 H, J = 7.6 Hz), 7.31 (dt, 1 H, J = 1.2, 7.1 Hz), 1.44 (s, 6H).
Step E (a-2- (2- (2-y2- (4-trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -propan-2-ol To a mixture of Compound 10e (11.7 g, 71 mmol), Compound 10c (19.9 g, 54 mmol), sodium carbonate (46 g, 435 mmol) and PdCI2 (dppf) * CH2Cl2 (8.9 g, 11 mmol) in a 1 liter balloon equipped with a water coolant were added 400 ml. of DME anhydrous and 200 ml of water. The mixture was evacuated and filled with argon three times. The mixture was heated at 100 ° C for 20 h. The mixture was then cooled to room temperature. The biphasic system was transferred to a 1 liter separating funnel and the two phases separated. The organic phase was washed with brine (2 x 300 mL). The aqueous phases were combined and extracted with ethyl acetate (approximately 300 ml). The organic phases were combined, dried with sodium sulfate and filtered. The volume of the filtrate was reduced to approximately 170 ml at reduced pressure. The mixture was then filtered through a pad of silica gel and the pad was washed with ethyl acetate until the filtrate contained no product. After concentration, a light pink / beige solid was obtained. The solid was triturated with 50 ml of ethyl d-acetate and the mixture was heated at 85 ° C for 5 min. The mixture was slowly added to rt, then cooled to 0 ° C for 0.5 h. The mixture was filtered and the solid was washed twice with cold ethyl acetate and dried under vacuum at 40 ° C to yield the title compound 18 as a light beige solid (7.58 g, 33%). RP-HPLC 95% purity. 1 H NMR (400MHz, DMSO-d 6) d (ppm): 12.73 (m, 1 H,), 7.90 (d, 2H, J = 8.2 Hz), 7.85 (dd, 1 H, J = 8.0, 0.6 Hz), 7.78 (d, 2H, J = 8.4 Hz), 7.74 (d, 1 H, J = 16.8 Hz), 7.59-7.47 (m, 1 H), 7.41 (s, 1 H), 7.37-7.32 (m, 2H), 7.21 (dt, 1 H, J = 1.2, 7.4 Hz), 7.06 (s, 1 H), 7.02 (d, 1 H, J = 7.4 Hz), 4.85 (s, 1 H), 1.21 (s, 6H).
Mass spectrum (LCMS, APCI pos.) Calculated for C25H21 F3N2O: 423.2 (M + H), Experimental 423.3. P.F. (uncorr.) 250-251 ° C.
Through the procedures disclosed in Example 10 and the corresponding reagents, starting materials and known conditions those skilled in the art, the following compounds were prepared representative of the present invention: Comp. Name and data 23 (£) -2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -H-benzimidazol-5-yl.} - phenyl) -propan-2- ol 1H-NMR (400 MHz, DMSO d6) d (ppm) 7.84 (dd, J = 1.26, 8.084Hz, 1 H) 7.75-7.85 (m, 2H) 7.66 (d, J = 16.4Hz) 7.53-7.58 ( m, 1 H) 7.45 (bs, 1 H) 7.34-7.38 (m, 3H) 7.17-7.26 (m, 3H) 7.09 (dd, J = 1.58, 7.58Hz, 1 H) 1.36 (s, 6H). MS (ESI, pos. Ion) miz: 439.2 (M + 1). 47 (E) -2- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol 1H NMR (400MHz, CD3OD) d (ppm): 8.07 (d, 2H, J = 8.6 Hz), 7.98 (d, 2H, J = 8.6 Hz), 7.78 (dd, 1 H, J = 1.1, 8.1 Hz), 7.69 (d, 1 H, J = 16.5 Hz), 7.54 (d, 1 H, J = 8.2 Hz), 7.44 (d, 1 H, J = 16.5 Hz), 7.42 (br s, 1 H), 7.31 ( ddd, 1 H, J = 1.5, 7.8, 8.1 Hz), 7.18 (dt, 1 H, J = 1.3, 7.4 Hz), 7.16 (dd, 1H, J = 1.5, 8.3 Hz), 7.03 (dd, 1H, J = 1.4, 7.5 Hz), 1.31 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C25H2iF3N203S: 487.1 (M + H), Experimental 487.1.
Comp. Name and data 78 (E) -2- (2- { 2- [2- (4-chloro-phenyl) -v] nyl] -1 H- benzimidazol-5-yl.} - phenyl) -propan-2-ol 1 H NMR (400 MHz, CD 3 OD) d (ppm): 7.79 (dd, 1 H, J = 8.1, 1.1 Hz), 7.63-7.54 (m, 3H), 7.51 (br d, 1 H , J = 9.7, 7.4 Hz), 7.40-7.38 (m, 3H), 7.31 (m, 1 H), 7.19 (dt, 1 H, J = 1.4, 7.4 Hz), 7.15 (d, 1 H, J = 16.5 Hz), 7.13 (dd, 1 H, J = 7.9, 1.8 Hz), 7.04 (dd, 1 H, J = 7.5, 1.4 Hz), 1.30 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C24H21CIN20: 389.1 (M + H), Experimental 389.3. 84 (E) -2- (2- { 2- [2- (4-methanesulfonyl-pheny] -vinyl] -1 H -benzyldazol-5-yl.} - phenyl ) -propan-2-ol 1H-NMR (400 MHz, CD3OD) d (ppm): 8.00 (d, J = 8 Hz, 2H), 7.91 (d, J = 8 Hz, 2H), 7.82 (dd, J = 1.6, 8 Hz, 1 H), 7.70 (d, J = 16.4 Hz, 2H), 7.41 (s, 1 H), 7.36 (dt, J = 1.6, 8 Hz, 1 H), 7.34 (s, 1 H), 7.23 (dt, J = 1.6, 8 Hz, 1 H), 7.19 (dd, J = 1.6, 8 Hz, 1 H), 7.07 (dd, J = 1.6, 8 Hz, 1 H), 3.16 (s, 3H), 1.26 (s, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C25H24 2O3S: 433.1 (M + H), Experimental 433.4. 114 (E) -2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol H NMR (400 MHz, CD3OD) d (ppm): 7.89-7.87 (m, 2H), 7.79 (dd, 1 H, J = 8.1, 1.1 Hz), 7.67-7.56 (m, 3H), 7.52 (m, 1 H), 7.40 (br s, 1 H), 7.31 (m, 1 H), 7.27 (d, 1 H, J = 16.6 Hz), 7.18 (dt, 1 H, J = 1.3, 7.4 Hz), 7.14 ( dd, 1 H, J = 8.3, 1.4 Hz, 1 H), 7.04 (dd, 1 H, J = 7.52, 1.38 Hz), 1.31 (s, 6H). LCMS mass spectrum, APCI pos.) Calculated for C25H2iF3N20: 423.2 (M + H), Experimental 423.3. 458 (E) -2.2,2-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. L) - acetamide. The title compound (0.0195 g) was prepared from Compound 465 (0.10 g, 0.26 mmole) and trifluoroacetylimidazolide (0.047 g, 0.29 mmole). 1 H-NMR (400 MHz, DMSO d 6) d (ppm): 12.7-12.9 (bs, 1 H) 1 1.0 (s, 1 H) 7.90-7.94 (d, J = 8.59Hz, 2H)) 7.78-7.81 ( d, J = 8.59Hz, 2H) 7.37-7.76 (m, 7H) 7.20 (d, J = 9.34Hz, 1 H) MS (ESI, pos. ion) m / z: 476.2 (M + 1). 459 (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (E) -2.2.2 - trifluoro-ethanesulfonic The title compound (0.0015 g) was prepared from Compound 465 (0.034 g, 0.09 mmol) and trifluoromethylsulfonyl chloride (0.018 g, 0.10 mmol). H NMR (400 MHz, DMSO d6) d (ppm) 12.75-12.82 (bs, 1 H) 9.70-9.80 (bs, 1 H) 7.90-7.96 (d, J = 8.08Hz, 2H) 7.78-7.84 (m , 3H) 7.54-7.77 (m, 2H) 7.40-7.50 (m, 2H) 7.24-7.40 (m, 6H) 4.0 (bs, 2H) MS (ESI, pos. Ion) m / z: 526.1 (M + 1 ).
Comp. Name and data 460 (£) -2.2-D-benzimidazole- (2- { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1 H-benzimidazole -5-yl.}. phenyl) -propionamide the title compound (0.0014 g) was prepared from compound 465 (0.034 g, 0.09 mmol) and trimethylacetyl chloride (0.012 mi, 0.036 mmol). H-NMR (400 MHz, CD3OD) d (ppm) 7.80-7.84 (m, 3H) 7.58-7.78 (m, 6H) 7.38-7.42 (m, 2H) 7.24-7.35 (m, 3H) 1.20 (s, 9H ) MS (ESI, pos. Ion) / z: 464.3 (M + 1). 461 (2- {2- [2- (4-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (£) -ethanesulfonic acid The title compound (0.0018 g) was prepared from Compound 465 (0.10 g, 0.26 mmol) and ethylsulfonyl chloride (0.027 mL, 0.29 mmol). H-NMR (400 MHz, DMSO d6) d (ppm) 12.88 (d, J = 9.1 Hz, 1 H) 8.92 (d, J = 7.3 Hz, 1 H) 7.78 (d, J = 8.08 Hz, 2 H)) 7.85 (d, J = 8.08Hz, 2H) 7.72-7.82 (m, 3H) 7.63-7.68 (m, 1 H) 7.30-7.53 (m, 6H) 2.78-2.92 (qq, J = 7.33Hz, 2H) 1.00 (tt, J = 7.33Hz, 3H). MS (ESI, pos. Ion) m / z: 472.1 (M + 1). 462 (£) - (2- { 2 .- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -carbamic acid methyl ester The compound of the title (0.0056 g) was prepared from Compound 465 (0.10 g, 0.26 mmol) and chloromethyl formate (0.022 ml, 0.29 mmol). 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 7.82-7.84 (d, J = 8.59 Hz, 2 H) 7.76-7.78 (d, J = 8.59 Hz, 2 H) 7.62-7.70 (m, 3 H) 7.59 ( bs, 1 H) 7.36-7.41 (m, 3H) 7.24-7.34 (m, 3H). MS (ESI, pos. Ion) m / z: 438.4 (M + 1). 463 (£) -2- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 7.82- 7.84 (m, 1 H) 7.35-7.64 (m, 8H) 7.10-7.30 (m, 4H) 1.38 (s, 15H). MS (ESI, pos. Ion) m / z: 41 1.3 (M + 1). 465 (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} phenylamine The title compound was prepared from Compound 479 by stirring in TFA with heating. 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 12.78 (s, 0.5 H) 12.75 (s, 0.5 H) 7.91 (d, J = 8.08 Hz, 2 H) 7.78- 7.81 (m, 3 H) 7.74 (d , J = 4.55Hz, 1 H) 7.68 (d, J = 8.08Hz, 1 H) 7.56-7.62 (m, 1 H) 7.52 (bs, 1 H) 7.41 (d, J = 16.4Hz, 1 H) 7.20 -7.29 (m, 1 H) 7.05 (t, J = 7.6Hz, 2H) 6.78 (d, J = 8.34Hz, 1 H) 6.65 (t, J = 6.8Hz, 1 H) 4.81 (s, 1 H) 4.74 (s, 1 H) MS (ESI, pos. Ion) m / z: 526.1 (M + 1).
Comp. Name and data 466 ethyl ester of (E) -2- acid. { 2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzoic acid 1H-NMR (400 Hz, D SO d6) d (ppm) 7.82- 7.84 (d, J = 8.59Hz, 2H) 7.76-7.78 (d, J = 8.59Hz, 2H) 7.62-7.70 (m, 3H) ) 7.59 (bs, 1 H) 7.36-7.41 (m, 3H) 7.24-7.34 (m, 3H). MS (ESI, pos. Ion) m / z: 438.4 (M + 1). (£) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol 1 H-NMR (400 MHz, CD3OD) d (ppm) 8.18 (bs, 2H) 7.70 (m, 3H) 7.44 (m, 3H) 7.30 (m, 3H) 7.22 (m, 2H) 7.19 (m, 1 H) 1.28 (s, 9H). MS (ESI, pos. Ion) m / z: 412.2 (M + 1) (E) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - phenyl) sulfamide The title compound (0.0023 g ) was prepared from Compound 465 (0.0175 g, 0.046 mmol) and sulfamide (0.5 g, 5.2 mmol). 1 H NMR (400 MHz, DMSO d 6) d (ppm) 7.86 (d, J = 8.61 Hz, 2 H) 7.62-7.78 (m, 6 H) 7.31- 7.41 (m, 4 H) 7.21-7.25 (m, 1 H) . MS (ESI, pos. Ion) m / z. 459.2 (M + 1). (E) - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -methanol 1 H-NMR (400 MHz, CD3OD ) d (ppm) 7.83 (d, J = 8.59Hz, 2H) 7.77 (d, J = 8.34Hz, 2H) 7.56-7.74 (m, 5H) 7.24-7.42 (m, 5H) 4.56 (s, 2H) MS (ESI, pos. Ion) m / z: 395.1 (M + 1). (E) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -acetamide 1H-NMR (400 MHz , CD3OD) d (ppm) 7.80- 7.84 (m, 3H) 7.56-7.78 (m, 5H) 7.30-7.44 (m, 5H) 1.97 (s, 3H). MS (ESI, pos. Ion) m / z: 422.3 (M + 1). (£) - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl] -carbamic acid tert-butyl ester H -NRM (400 MHz, CD3OD) d (ppm) 7.76-8.00 (d, J = 8.1 Hz, 2H) 7.82-7.90 (d, J = 8.8Hz, 2H) 7.68-7.79 (m, 4H) 7.36-7.48 ( 5H) 1.44 (s, 9H). MS (ESI, pos. Ion) m / z: 480.2 (M + 1). 480 (E) -5- (2-methylsulfanyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole 1H-NMR (400 MHz, CD3OD) d (ppm) 7.84-7.87 (d, J = 8.1 Hz, 2H) 7.56-7.78 (m, 5H) 7.20-7.40 (m, 6H). MS (ESI, pos. Ion) m / z: 41 1.2 (M + 1).
Comp. Name and data 481 (£) -2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -5- (2-trifluoromethyl-phenyl) -1 H -benzimidazole 1 H NMR (400 MHz, CD3OD) d (ppm) : 8.10 (d, 2H, J = 8.5 Hz, 1H), 8.02 (d, 2H, J = 8.5 Hz), 7.77 (d, 1H, J = 7.8 Hz, 1 H), 7.73 (d, 1 H, J = 16.5 Hz), 7.64 (d, 1 H, J = 7.4 Hz), 7.60 (d, 1 H, J = 8.4 Hz), 7.54 (d, 1H, J = 7.7 Hz), 7.50 (s, 1 H) , 7.46 (d, 1H, J = 16.5 Hz), 7.42 (d, 1 H, J = 7.6 Hz), 7.22 (dd, 1 H, J = 8.4, 1.0 Hz). Mass spectrum (LCMS, APCI pos.) Calculated for C23H14F6N202S: 497.1 (M + H), Experimental 497.1. 482 (E) -2- (2- { 2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.00-7.94 (m, 2H), 7.79 (dd, 1 H, J = 8.1, 1.1 Hz), 7.73 (d, 1 H, J = 7.9 Hz) , 7.66 (t, 1 H, J = 7.7 Hz), 7.53 (br s, 1 H), 7.50 (t, 1 H, J = 7.67, 7.67 Hz), 7.41 (br s, 1 H), 7.31 (m , 1 H), 7.21-7.13 (m, 3H), 7.04 (dd, 1 H, J = 7.5, 1.4 Hz), 1.31 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C25H21F3N20: 423.2 (M + H), Experimental 423.3. 483 (E) -dimethyl- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzyl) -amine To a solution of the Compound 484 (20.7 mg, 0.053 mmol) in DMF (10 mL) was added 2.0 M dimethylamine in THF (66 μ ?, 0.132 mmol). The mixture was stirred for 45 min and sodium triacetoxyborohydride (17 mg, 0.080 mmol) was added. The mixture was stirred at rt for 2.5 d and then concentrated under reduced pressure. The residue was purified by preparative TLC plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes: methanol 5: 5: 1) to give the title compound (18.2 mg, 81%). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 7.81 (d, 2 H, J = 8.2 Hz), 7.70 (d, 2 H, J = 8.0 Hz), 7.67 (d, 1 H, J = 16.3 Hz), 7.60 (d, 1 H, J = 8.2 Hz), 7.55-7.47 (m, 2H), 7.40-7.26 (m, 4H), 7.19 (dd, 1 H, J = 8.3, 1.5 Hz), 3.58 (s, 2H), 2.14 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C25H22F3N3: 422.2 (M + H), Experimental 422.1. 484 (F) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzaldehyde H NMR (400 MHz, DMSO-d6) d (ppm): 12.93 (d, 1 H, J = 12.5 Hz), 9.93 (s, 1 H), 7.93 (d, 3H, J = 8.4 Hz), 7.82-7.56 (m, 8H), 7.44 (d, 1 H, J = 16.5 Hz), 7.28 (dd, 1 H, J = 10.1, 9.3 Hz). Mass spectrum (LCMS, APCI pos.) Calculated for C23H15F3N20: 393.1 (M + H), Experimental 393.3.
Comp. Name and data 485 (E) -methyl- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzyldazole-5-ii. benzyl) -amine The title compound was prepared according to the procedure used for Compound 483, with the exception that methylamine was employed. 1 H NM (400 MHz, CD 3 OD) d (ppm): 7.82 (d, 2 H, J = 8.3 Hz, 1 H), 7.71 (d, 2 H, J = 8.3 Hz), 7.69 (d, 1 H, J = 16.6 Hz), 7.63 (d, 1 H, J = 8.1 Hz), 7.52-7.47 (m, 2H), 7.39 (tdd, 2H, J = 9.1, 7.2, 3.6, 3.6 Hz), 7.35-7.29 (m, 2H ), 7.23 (dd, 1 H, J = 8.3, 1.6 Hz), 3.86 (s, 2H), 2.30 (s, 3H). Mass spectrum (LCMS, APCI pos.) Calculated for C24H20F3 3: 408.2 (M + H), Experimental 408.1. 487 (E) -5- (2-trifluoromethyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole 1H NMR (400 MHz, CD3OD) d (ppm): 7.80 ( d, 2H, J = 8.2 Hz), 7.76 (d, 1 H, J = 7.9 Hz), 7.70-7.60 (m, 4H), 7.57 (d, 1 H, J = 8.3 Hz), 7.52 (t, 1 H, J = 7.7 Hz), 7.47 (s, 1 H), 7.40 (d, 1 H, J = 7.6 Hz), 7.29 (d, 1 H, J = 16.6 Hz), 7.19 (dd, 1 H, J = 8.3, 1.0 Hz). Mass spectrum (LCMS, APCI pos.) Calculated for C23H14F6N2: 433.1 (M + H), Experimental 433.3. 488 (£) -5- (2-trifluoromethoxy-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -H-benzimidazole 1 H NMR (400 MHz, CD3OD) d (ppm): 7.78 (d , 2H, J = 8.3 Hz), 7.68-7.66 (m, 3H), 7.63-7.58 (m, 2H), 7.50 (m, 1 H), 7.43-7.35 (m, 3H), 7.33 (dd, 1 H , J = 8.4, 1.6 Hz), 7.27 (d, 1 H, J = 16.6 Hz). Mass spectrum (LCMS, APCI pos.) Calculated for C23Hn4F6N20: 449.1 (M + H), Experimental 449.3.
EXAMPLE 10.1 Scale preparation of (E) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol (Comp 18) Step A 3- (4-trifluoromethyl-phenyl) -acrylic acid A 2-liter four-neck balloon equipped with an air cooler / argon inlet, mechanical stirrer, thermocouple and a stopper was charged with 4- (trifluoromethyl) benzaldehyde (250 g, 196.2 ml, 1.44 moles), malonic acid (302.6 g, 2.87 moles), and pyridine (750 ml). An exotherm (approximately 38-40 ° C) was developed, which was maintained for 30 min. Then piperidine (14.202 ml, 143.58 mmol) was added to the reaction and a second exotherm was developed (Tmax about 42 ° C after about 10 min.). The reaction was stirred for 30 min and then heated at 60 ° C for 18 h (overnight). The reaction appeared to be complete by TLC, and cooled to approximately 40 ° C, diluted in water (2 I; performed to prevent freezing of the reaction), cooled to room temperature and further diluted with water (4 liters, total 6 liters). The suspension was acidified to pH = 2.0-3.0 with concentrated hydrochloric acid (approximately 675-700 ml). The material was stirred for 30 min., And a white solid was collected by filtration. The filter cake was washed with water until the filtrate was neutral (pH about 5.5-6, 2.5 I), air dried in a Buchner funnel for 2 h, and then further dried in a vacuum oven at 60 ° C. ° C over night to give 300.5 g (96%) of the title compound 10a as a white solid.
Step B (E) -5-bromo-2- [2- (4-trifluoromethyl-phenyl) -vinn-1 H-benzimidazole To a 4-nozzle, 5-liter balloon provided with a magnetic stirrer, inlet of argon / argon outlet to a carbonate brush, two stoppers and a water bath at room temperature was charged with 4- (trifluoromethyl) cinnamic acid (315 g, 1.46 moles) and dichloromethane (3.15 I) to provide a suspension. To the suspension was added oxalyl chloride (151.71 ml, 1.75 moles) and DMF (1.13 ml, 14.57 mmol). After the addition of DMF, the gas development began and the reaction continued for about 3 h, during which time a solution was developed. When the reaction was complete (LC-MS), it was concentrated to dryness to provide 342.4 g of the 3- (4-trifluoromethyl-phenyl) -acyloyl chloride, Compound 10b (> 100%), as a yellow oily solid. A four-liter 5-liter balloon equipped with a mechanical stirrer, thermocouple, air coolant with argon inlet and a stopper was charged with 4-bromo-benzene-1,2-diamine (244 g, 1.27 mol) and acetic acid (2.13 liters) ). To this solution was added a solution of Compound 10b (327 g, 1.39 moles) in toluene (237 ml). After this addition, the temperature was increased to 45 ° C in about 30 seconds and then lowered. The reaction was then heated at 90 ° C for 16 h (overnight). The reaction was cooled to 40 ° C, and poured into a mixed solution of EtOAc and heptane (approximately 1: 3, 5.75 liters) and a precipitate was produced. The resulting suspension was stirred for 3 h, and the solid was collected by filtration, washed with EtOAc: heptane (1: 3, 3 liters, and then dried in a vacuum oven (60 ° C) to provide 324.3 g ( 65%) of the title compound 10c as a partial acetate salt.
Step C 2- (2-bromo-phenyl) -propan-2-ol A 12-liter 4-neck balloon provided with a thermocouple, condenser, septum, addition funnel and upper mechanical agitator under argon was charged with methyl-2-bromobenzoate ( 226.5 g, 1.05 moles) and THF (1.6 I, 19.66 moles). The mixture was cooled to a temperature between 2 and 5 ° C with stirring and maintained for 30 min. To the solution was slowly added methyl magnesium bromide in dylethylether (3M, 1.05 liters, 3.15 moles) by means of an addition funnel at a rate to maintain the reaction temperature below 15 ° C. An exotherm was observed during the addition, the reaction temperature was heated to 3 to 15 ° C. The addition of 1.05 liters of Grignard was completed in 4 h (the approximate feed rate was 4.17 ml / min). The reaction mixture appeared as a white / yellow suspension. The reaction was allowed to warm to room temperature and was stirred overnight (15 h). The reaction was sampled by HPLC / TLC and showed no starting material present. The ice bath was again applied to the reaction flask and a solution of 0.5 M HCl (4.5 liters, 2.25 moles) was added slowly over a period of 2 h. The temperature increased dramatically from 0 to 15 ° C. After the inactivation was complete, the reaction was stirred at room temperature for 30 min. Additional 2 N HCl (500 ml, 1.00 moles) was added slowly to maintain a pH of less than 6. MTBE (1 liter) was added to aid phase division. The reaction was stirred at room temperature for 1 to 2 h to dissolve the solid material in an aqueous phase (most likely Mg (OH) 2 which is very basic). The pH should be examined and adjusted with additional acid when necessary. The phases were separated and the aqueous phase was washed with an additional 1 liter of MTBE (2 x 500 ml). The organic phases were combined, washed with a solution of NaHCO 3 on (2 x 300 mL), dried with MgSO 4, filtered and the filtrate was concentrated in vacuo to yield the title compound 10d (220.83 g, 97.48% yield) as a light yellow oil.
Step D 3. 3-dimethyl-3H-benzorcin .21-oxaborol-1 -ol A 12-liter 4-neck balloon provided with a thermocouple, condenser, septum, addition funnel and overhead mechanical stirrer under argon was charged with anhydrous THF, (3 liters) and cooled to -70 to -78 ° C by means of a dry ice / acetone bath. N-Butyl lithium (2.5 N in hexanes, 860 ml, 2.15 moles) was slowly added via an addition funnel. An exotherm was observed as the temperature rose from -78 to -70 ° C. To the addition funnel was added a solution of Compound 10d (220 g, 979.97 mmol) in anhydrous THF (1 liter). The solution of 2- (2-bromophenyl) propan-2-ol was slowly added to the solution of n-BuLi. The addition took 90 minutes in order to maintain a reaction temperature below -70 ° C. After the addition was complete, the reaction mixture was stirred at -70 to -75 ° C for 30 min. The triethylborate (230 ml, 1.35 moles) was added rapidly in 3 portions at -70 ° C. An exotherm was observed, the batch temperature was raised from -70 to -64 ° C. The reaction was stirred at -70 ° C and slowly warmed to room temperature overnight. After the reaction was cooled to 0-5 ° C, the reaction was slowly quenched with 2 M HCl (1 liter, 2.00 moles) added via the addition funnel while maintaining the batch temperature at 0-5 ° C. . The reaction mixture was stirred for 1 h. The pH of the aqueous phase pH was 9-10. Then the pH was adjusted to acid (4-5) with 2 M HCl (200 ml). The two phases were separated and the aqueous phase was extracted with MTBE (2 x 500 mL). The combined organic phases were dried with anhydrous magnesium sulfate. The solution was filtered and concentrated to produce a yellow oil. The yellow oil was diluted with MTBE (1.5 liter) and washed with 1 M NaOH (3 x 500 ml). The aqueous phases containing the product were combined and acidified with 2M HCl (800 ml) (the clear solution becomes cloudy with the addition of acid). After stirring the cloudy solution for 15 min (pH = 4-5) (Note 1), it was extracted with MTBE (2 x 500 ml). The organic phases were combined and dried with MgSO 4. The solution was filtered and the filtrate was concentrated to yield the title compound 10e as a light yellow oil (121.78 grams, 77% yield).
Step E (E) -2- (2- (2-r2- (4-Trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -propan-2-ol A four-mouth balloon of 5 liters provided with a thermocouple controller, coolant, mechanical agitator on top, Firestone® valve and a nitrogen inlet / outlet was charged with dimethoxyethane (2 liters), DI water (1 liter) and sodium carbonate (230.9 g) , 2.18 moles). The solution was degassed and purged with N2 three times. Compound 10e (71.7 g, 0.35 moles) and Compound 10c (100.0 g, 0.27 moles) were added to the degassed solution. The solution was degassed and purged with N2 three times. PdCl2 (dppf) (44.48 g, 54.4 mmol) was added to the solution and the solution was degassed and purged with N2 three times. The resulting two-phase suspension was heated to reflux for 18 h, and then cooled to room temperature. The reaction mixture was transferred to a 12 liter decant funnel, and the phases were separated. The organic phase was washed with brine (1 liter). The two aqueous phases were combined and extracted with EtOAc (1 liter). The combined organic phases were dried (Na2SO4), filtered and the filtrate was concentrated to an oil. Two coupling reactions of 100 g separately were combined and purified by chromatography in 10 successive chromatographic runs in an ISCO preparative chromatography system (column 10 x 1.5 Kg SiO2, 5 volumes of EtOAc column, flow rate 250 ml / min). The combined fractions were transferred to 22-liter four-neck balloons and silica gel functionalized with Silicycle Si-thiol (2 g) was added to each solution. The solutions were heated to 40 ° C and stored for 1 h. The solutions were filtered through a medium glass funnel and washed with EtOAc (4 liter) and combined. The filtrate was evaporated to a semi-solid, which was transferred to a 2 liter balloon to which EtOAc (0.4 liter) was added. The suspension of the resulting white precipitate was cooled to -5 ° C and stirred for 1 h. The suspension was filtered and washed with cold EtOAc (100 mL). The solids were dried in a vacuum oven at 40 ° C for 40 h to provide 84.0 g (36.5% yield, 98.8% surface purity) of the title compound 18 as a white solid. Anal. Calculated for C25H2iN2OF3-0.04% H2O 0.15 moles MeOH: C, 70.48; H, 5.14: N, 6.42; F, 13.06 Experimental: C, 70.54; H, 4.83: N, 6.18; F, 13.33 EXAMPLE 10.2 Monosodium salt of (E) -2- (2- ^ 2-r2- (4-trifluoromethyl-phenyl) -vinyl-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol ( Comp 18) A five-liter four-neck balloon equipped with a thermocouple controller, a mechanical stirrer at the top and a nitrogen inlet / outlet was charged with Compound 18 (E) -2- (2-. {2- 2- [ 2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol (125.0 g, 0.510 mol) and MeOH (1.25 liters). A solution of sodium methoxide in methanol (0.5 M, 592 ml, 0.3 moles) was added. The reaction was heated at 65 ° C for 30 min and all solids dissolved. The solution was cooled and evaporated to dryness. The foam was collected by removing the flask. The solids were placed in a vacuum oven for 24 h at 40 ° C to give 139 g (approximately 100% isolated yield) of the monosodium salt of the title compound 18 as a yellowish solid. 1 H NMR (400MHz, DMSO-d 6) d 7.80-7.84 (m, 3H), 7.74 (d, 2H, J = 8.59 Hz), 7.65 (d, 1 H, J = 16.4 Hz), 7.40-7.44 (m, 2H), 7.25-7.37 (m, 2H), 7.16-7.20 (m, 1 H), 7.01-7.05 (m, 1 H), 6.84-6.87 (m, 1 H), 1.23 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C25H21 F3N2O: 423.2 (M + H), Experimental 423.3. P.F. (not corrected) 258-259 ° C.
EXAMPLE 10.3 (E) -2- (2 2 -R2- (4-Trifluoromethyl-phenyl) -vinyl-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol d-hydrochloride salt fComp. 18) A 250 ml decanting ampoule was charged with Compound 18 (E) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol (1.0 g, 2.4 mmol) and EtOAc (20 mL). Aqueous HCl (1M, 20 ml) was added to the white suspension, and the separating funnel was stirred. The solid product dissolved rapidly, and a white precipitate began to form. The organic phase was transferred to a 100 ml balloon equipped with a magnetic stirrer and stirred for 2 h. The slurry was filtered, rinsed with EtOAc (2 x 5 ml), and placed in a vacuum oven at 40 ° C for 36 h to provide 0.95 g (87.5%) of the title compound 18 as the hydrochloride salt.
EXAMPLE 11 (E) -2-f2-r2- (4-tert-butyl-phenyl) -v-n-n-6-trifluoromethyl-1H-benzimidazol-5-yl) -phenol (Compound 48) ) Step A N- (4-bromo-2-nitro-5-trifluoromethyl-phenyl) -2,2,2-trifluoroacetamide 4-bromo-3-trifluoromethyl aniline (4.8 g, 0.02 mol) was added in portions to a stirred trifluoroacetic anhydride and cooled with ice (50 ml). To the resulting solution was added KNO3 (2.22 g, 0.022 mol, 1.1 eq) in portions. The reaction mixture was stirred at 0 ° C for 1 h, and then allowed to warm to room temperature overnight. The reaction mixture was diluted with ice water (150 ml), and the solid was collected by vacuum filtration. The solid was washed with water (50 ml) and dried vacuo to give the title compound 11a as a bright yellow solid (6.4 g). 1 H-NMR (400MHz, CDCl 3) d (ppm): 9.19 (s, 1 H) 8.64 (s, 1 H) MS (ESI, pos. Ion) m / z: 381.4 (M + 1).
Step B 4-bromo-2-nitro-5-trifluoromethyl-phenylamine Compound 11a (5.7 g, 0.015 mol) was dissolved in a mixture of methanol (25 ml) and saturated aqueous solution of K2CO3 (15 ml). The reaction mixture was then stirred at room temperature for 10 h. The reaction mixture was diluted with water (25 ml) and the product was collected by vacuum filtration to provide the title compound 11 b as a yellow solid (2.99 g). 1 H-NMR (400MHz, CDCl 3) d (ppm): 8.44 (s, 1 H) 7.21 (s, 1 H), 6. 21 (bs, 2H). MS (ESI, pos. Ion) m / z: 285.0 (M + 1).
Step C 4-Bromo-5-trifluoromethyl-benzene-1,2-diamine Compound 11 b (2.85 g, 0.01 mol) was dissolved in 30 ml of ethanol. Zinc powder (5.9 g, 0.09 mole) was added in portions followed by the addition of ammonium chloride (1.07 g, 0.02 mole, 2 eq). The reaction mixture was stirred at room temperature overnight (16 h). The reaction mixture was filtered on a pad of celite and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (40 ml), washed with 35 ml of brine, dried with Na 2 SO 4, and evaporated in vacuo. The residue was purified by chromatography (silica gel, CH2Cl2: MeOH, 96: 4-94: 6)) to give the title compound 11c as a bright yellow solid (1.53 g), which was used without further purification in the next He passed. H-R N (400MHz, CD3OD) d (ppm): 6.99 (s, 1 H) 6.92 (s, 1 H) MS (ESI, pos ion) m / z: 254.7 (M + 1).
Step D (-5-bromo-2- [2- (4-tert-butyl-phenyl) -vinyl-6-trifluoromethyl-1H-benzimidazole 4-f-butyl acrylic acid was dissolved (1.02 g, 0.0055, 1.1 eq ) in 30 mL of POCI 3. To this solution was added Compound 11c (1.27 g, 0.005 mole), and the reaction mixture was heated to reflux for 6 h (The reaction mixture was quite dark). it was cooled to room temperature and concentrated in vacuo.The residue was taken up in 50 ml of ethyl acetate, washed with 50 ml of brine, dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. chromatography (silica gel, hexanes: EtOAc, 1: 3-2: 3) to provide the title compound 11d as a light brown solid (0.84 g) H-NMR (400MHz, CDCl 3) d (ppm): 7.91 ( d, 2H, J = 18.5 Hz) 7.69 (d, 1 H, J = 16.4 Hz), 7.32 (m, 4H) 7.09 (d, 1 H, J = 16.5 Hz) 1.28 (s, 9H) MS (ESI , ion pos.) m / z: 423.7 (M + 1).
Step E (E) -2- (2-2 2 - (4-tert-butyl-phenyl) -vinyl-6-trifluoromethyl-1 H-benzimidazol-5-yl) -phenol Compound 11d (0.00026 moles, 0.10 g) was dissolved in 5 ml of dioxane. 2-Hydroxyphenyl boronic acid (0.00052 mol, 0.072 g, 2.0 equiv) was added followed by aqueous Na2CO3 (0.00055 mol, 0.28 ml of 2M solution) and dichlorobis (tricyclohexylphosphino) -palladium (II) (0.01 g, 6 mol%) ). The reaction mixture was heated on a microwave synthesizer at 1 10 ° C for 20 minutes. The reaction mixture was cooled and the solvent was concentrated in vacuo. The residue was taken up in 10 ml of CH 2 Cl 2, and washed successively with 10 ml of saturated aqueous NaHCO 3 solution and 10 ml of brine. The organic fractions were dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, CH 2 Cl 2: MeOH, 98: 2-95: 5) to provide the title compound 48 as a white solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 7.29-7.56 (m, 8H) 7.15 (d, 1 H, J = 6.7 Hz) 6.89-7.05 (m, 3H)) 1.34 (s, 9H). MS (ESI, pos. Ion) m / z: 437.1 (M + 1). By the procedures described in Example 11 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data (£) -3-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl} -phenol The title compound was prepared from 3-hydroxyphenyl boronic acid (0.00052 mol, 0.072 g) and Compound 1a (0.00026 mol, 0.10 g). H-R N (400 MHz, CDCl 3) d (ppm): 7.25-7.61 (m, 8H) 7.19 (d, 1 H, J = 7.0 Hz) 6.90-7. 1 (m, 3H)) 1.28 (s, 9H). MS (ESI, pos. Ion) m / z: 437.1 (M + 1). (£) -N- (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl} -phenyl) Acetamide The title compound was prepared from 2-acetamidophenyl boronic acid (0.00052 mol, 0.093 g) and Compound 1a (0.00026 mol, 0.10 g) to provide the product as a white solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 8.15 (d, 2 H, J = 8.1 Hz) 7.73-7.76 (m, 2 H) 7.35-7.52 (m, 4 H) 7.0-7.14 (m, 3 H) 6.77 (s, 1 H) 1.45 (s, 9H) 1.35 (s, 3H). MS (ESI, pos. Ion) m / z: 478.2 (M + 1). (£) - (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzyl-aidazol-5-yl} -phenyl) -methanol The title compound was prepared from 2-hydroxymethyl phenyl boronic acid (0.00052 mol, 0.070 g) and Compound 1a (0.00026 mol, 0.10 g) to provide the product as a white solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 6.9-7.5 (m, 12H) 4.39 (m, 2 H) MS (ESI, pos. Ion) m / z: 451.2 (M + 1). (E) -2- [2- (4-tert-butyl-phenyl) -vinii] -5- (2-fluoro-phenyl) -6-trifluoromethyl-1H-benzimidazole The title compound was prepared from the acid 2-fluorophenylboronic acid (0.00052 mol, 0.073 g) and Compound 1a (0.00026 mol, 0.10 g) to provide the product as a beige solid. 1 H NMR (400 MHz, CDCl 3) d (ppm): 8.1 (m, 2 H) 7.72 (d, 2 H, J = 16 5 Hz) 7.42- 7.53 (m, 4 H) 7.05-7.20 (m, 4 H) 1.34 ( s, 9H). MS (ESI, pos. Ion) m / z: 440.1 (M + 1). (E) -2-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl} -benzamide The title compound was prepared from 2-aminocarbonyl phenylboronic acid (0.00052 mol, 0.086 g) and Compound 1a (0.00026 mol, 0.10 g) to provide the product as a yellow solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 7.2-7.8 (m, 9H) 6.91 (d, 2H, J = 5.4 Hz) 6.68 (d, 1 H, J = 19.5 Hz) 1.32 (s, 9H ). MS (ESI, pos. Ion) m / z: 465.25 (M + 1).
Comp. Name and data 54 ()) - (2- {2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl} -butyl ester .) phenyl) -carbamic The title compound was prepared from the t-butyl-N- [2-4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl) phenyl carbamate (0.00052 moles, 0.166 g) and Compound 1a (0.00026 moles, 0.10 g) to provide the product as a beige solid. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 8.0 (s, 1 H), 7.89 (s, 1 H), 7.62-7.79 (m, 4 H), 7.42-7.55 (m, 3 H), 7.36-7.41 (m, 2H), 7.15-7.30 (m, 2H))) 1.32 (s, 18H) MS (ESI, pos. Ion) m / z: 536.2 (M + 1). 55 (£) -N- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-H-benzimidazol-5-yl}. -phenyl) -methanesulfonamide The title compound was prepared from 2-methylsulfonylaminophenyl boronic acid (0.00052 moles, 0.1 1 1 g) and Compound 1a (0.00026 moles, 0.10 g) to give the product as a bright yellow solid. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 8.0 (s, 1 H) 7.79 (d, 1 H, J = 16.5 Hz) 7.65 (d, 2 H, J = 8.4 Hz) 7.5 (m, 3H) 7.41 (t, 1 H, J = 7.7 Hz) 7.23-7.28 (m, 3H) 7.10 (d, 1 H, J = 12.1 Hz) 2.5 (s, 3H) 1.31 (s, 9H). MS (ESI, pos. Ion) m / z: 514.2 (M + 1).
EXAMPLE 12 (E) -N- (2-6-trifluoromethyl-2-r2- (4-trifluoromethyl-phenin-vinin-1H-benzimidazol-5-yl-phenyl) -acetamide (Compound 56) Step A (E) -5-Bromo-6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazole By the procedure of Example 1 1, Step D, 4-trifluoromethyl acrylic acid (1.19 g, 0.0055, 1.1 eq) was dissolved in 30 ml of POCI3. TO This solution was added to Compound 11c (1.27 g, 0.005 mole), and the reaction mixture was heated to reflux for 6 h (The reaction mixture was quite dark). The reaction mixture was cooled to room temperature and then concentrated in vacuo. The residue was taken up in 50 ml of ethyl acetate, washed with 50 ml of brine, dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes: EtOAc, 3: 1-3: 2) to give the title compound 12a as a yellow solid (1.02 g). 1 H-NMR (400 MHz, CDCl 3) d (ppm): 7.92 (d, 2 H, J = 14.1 Hz) 6.67-7.76 (m, 5 H) 7.21 (d, 1 H, J = 16.5 Hz) MS (ESI, ion pos.) m / z: 368.3 (M + 1).
Step B (aN- (2- {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinin-1 H-benzimidazol-5-yl} -phenyl) -acetamide Compound 12a (0.00025 mol, 0.10 g) was dissolved in 5 ml of dioxane, 2-acetamidophenyl boronic acid (0.0005 mol, 0.089 g, 2.0 equiv) was added followed by aqueous Na2CO3 (0.00055 mol, 0.28 ml of a 2M solution) and dichlorobis (tricyclohexylphosphine) -palladium ( II) (0.01 g, 6 mol%) The reaction mixture was heated on a microwave synthesizer at 1 10 ° C for 20 min.The reaction mixture was cooled and the reaction mixture was concentrated in vacuo. The residue was taken up in 10 ml of CH 2 Cl 2, and washed successively with 10 ml of saturated aqueous NaHCO 3 solution and 10 ml of brine, The organic fractions were dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (gel silica CH2Cl2: MeOH, 98: 2-95: 5) to provide the title compound 56 as a white solid. 1 H NMR (400 MHz, DMSO-d 6) d (ppm): 8.68 (s, 1 H) 8.03 (s, 1 H) 7.80-7.96 (m, 6H) 7.35-7.50 (m, 3H) 7.20 (d, 2H, J = 4.1 Hz) 1.8 (s, 3H) MS (ESI, pos. Ion) m / z: 490.0 (M + 1).
Through the procedures described in Example 12 and the reagents, starting materials and conditions known to the experts in the art, the following representative Compounds of the present were prepared invention: Comp. Name and data 57 (£) -1 - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - ethanone The title compound was prepared from 2-acetylphenyl boronic acid (0.0005 mol, 0.082 g) and Compound 12a (0.00025 mol, 0.10 g) to provide the product as a yellow-white solid. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 7.81-8.0 (m, 8H) 7.42-7.62 (m, 3H) 7.30 (d, 1H, J = 6.8 Hz) 2.49 (s, 3H) MS (ESI, pos. Ion) m / z: 475.0 (M + 1). 58 (£) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) - methanol The title compound was prepared from 2-hydroxymethyl phenyl boronic acid (0.0005 mol, 0.067 g) and Compound 12a (0.00025 mol, 0.10 g) to provide the product as a light yellow powder. 1 H NMR (400 MHz, CDCl 3) d (ppm): 8.0 (d, 2 H, J = 8.1 Hz) 7.8 (d, 2 H, J = 8.2 Hz) 7.0-7.59 (m, 8 H) 4.91-5.07 (m, 1 H) 4.09-4.22 (m, 2H) (s, 9H). MS (ESI, pos. Ion) m / z: 463.0 (M + 1).
EXAMPLE 13 (a-2 6-Fluoro-2-r2- (4-trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenol (Compound 59) Step A N- (4-bromo-5-fluoro-2-nitro-phenyl) -2,2,2-trifluoroacetamide 4-bromo-3-fluoro-methyl-aniline (3.8 g, 0.02 mole) was added in portions to stirred trifluoroacetic anhydride cooled with ice (50 ml). To the solution was added KN03 (2.22 g, 0.022 moles, 1.1 eq) in portions. The reaction mixture was stirred at 0 ° C for 1 h and then allowed to warm to room temperature overnight. The reaction mixture was diluted with ice water (150 ml) and the solid was collected by vacuum filtration. The solid was washed with water (50 ml) and dried in vacuo to give the title compound 13a as a bright yellow solid (5.42 g) 1 H-NMR (400MHz, CDCl 3) d (ppm): 8.66 (d, 1 H , J = 10.0 Hz) 8.60 (d, 1 H, J = 1 1.3 Hz). MS (ESI, pos. Ion) m / z: 402.0 (M + Na).
Step B 4-bromo-5-fluoro-2-nitro-phenylamine Compound 13a (5.0 g, 0.015 mol) was dissolved in a mixture of methanol (25 ml) and saturated aqueous solution of K2CO3 (15 ml) and the mixture was stirred at room temperature. room temperature for 10 h. The reaction mixture was diluted with water (25 ml) and the product was collected by vacuum filtration to provide the title compound 13b as a yellow solid (2.5 g). H-NMR (400 MHz, CDCl 3) d (ppm): 8.39 (d, 1 H, J = 7.1 Hz) 6.75 (d, 1 H, J = 9.6 Hz) 6.19 (bs, 2H). MS (ESI, pos. Ion) m / z. 236.9 (M + 1).
Step C 4-Bromo-5-fluoro-benzene-1,2-diamine Compound 13b (1.88 g, 0.008 mol) was dissolved in 20 ml of ethanol. Zinc powder was added in portions (4.71 g, 0.072 mole) followed by the addition of ammonium chloride (0.86 g)., 0.016 moles). The reaction mixture was stirred at room temperature overnight (16 h). The reaction mixture was filtered with a pad of celite and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (30 mL) and washed with 25 mL of brine. The organic fractions were dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2: MeOH, 96: 4-94: 6)) to give title compound 13c as a dark yellow solid (1.02 g) which was immediately in the next reaction. MS (ESI, pos. Ion) m / z: 235.7 (M + 1).Step D (E) -5-bromo-6-fluoro-2-r2- (4-trifluoromethyl-phenyl) -vinn-1H-benzimidazole 4-trifluoromethyl cinnamic acid (1.2 g, 0.0055, 1.1 eq) was dissolved in 30 ml my from POCI3. To the solution was added Compound 13c (1.02 g, 0.005 mole), and the reaction mixture was heated to reflux for 6 h. The reaction mixture was cooled to room temperature and then evaporated in vacuo. The residue was taken up in 50 ml of ethyl acetate and washed with 50 ml of brine. The organic fractions were dried with Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes: EtOAc, 3: 1-3: 2) to give the title compound 13d as a light brown solid (0.80 g). 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 7.63-8.09 (m, 4 H) 7.4 (d, 1 H, J = 20.7 Hz) 6.69 (d, 1 H, J = 20.7 Hz) MS (ESI, pos. Ion) m / z: 386.0 (M + 1).
Step E (a-2- (6-fluoro-2-r2- (4-trifluoromethyl-phenyl) -vinin-H-benzimidazol-5-yl) -phenol Compound 13d (0.00025 mol, 0.096 g) was dissolved in 5 ml. dioxane, 2-hydroxyphenyl boronic acid (0.0005 mol, 0.069 g) was added followed by aqueous Na2CO3 (0.00055 mol, 0.28 ml of 2M solution) and dichlorobis (tricyclohexylphosphino) -palladium (ll) (0.01 g, 6% The reaction mixture was heated on a microwave synthesizer at 10 ° C for 20 minutes, the reaction mixture was cooled and the solvent evaporated in vacuo.The residue was taken up in 10 ml of CH 2 Cl 2, and the residue was taken up in 10 ml of CH 2 Cl 2. washed successively with 10 ml of saturated aqueous solution of NaHCO 3 and 10 ml of brine, the organic fractions were dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo, the residue was purified by chromatography (silica gel (CH 2 Cl 2: MeOH, 98%). : 2-95: 5) to provide the title compound 59 as a tan solid.1H-NMR (400 MHz, DMSO-d6) d (ppm): 7.90 (d, 2H, J = 8.0 Hz) 7.79 (d , 2H.J = 7.8 Hz) 7.22-7.53 (m, 4H) 6.88-6.96 (m, 4H) MS (ESI, pos. Ion) m / z: 399.1 (M + 1). By the procedures described in Example 13 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 60 (-3- {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} -phenol The compound of title was prepared from 3-hydroxyphenyl boronic acid (0.0005 mol, 0.069 g) and Compound 13d (0.00025 mol, 0.096 g) to give the product as a white solid.1H-RN (400 MHz, DMSO-d6) d (ppm): 7.76-8.0 (m, 4H) 7.24-7.64 (m, 5H) 6.96-7.03 (m, 1 H) 6.75-6.8 (m, 2H) MS (ESI, pos. ion) m / z: 399.3 (M + 1) .61 (£) - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. ) -methanol The title compound was prepared from 2-hydroxymethyl phenylboronic acid (0.0005 mole, 0.067 g) and Compound 13d (0.00025 mole, 0.096 g) to provide the product as a yellowish solid. H-NMR (400 MHz , CD30D) d (ppm): 7.83 (d, 2H, J = 8.2 Hz) 7.70-7.73 (m, 2H) 7.64 (t, 2H, J = 7.9, 7.5 Hz)) 7.55 (d, 1 H, J = 7.2 Hz) 7.25-7.46 (m, 4H) 7.10 (dd, 1 H, J = 1.2 Hz) 4.29 (d, 2H, J = 0.85 Hz) MS (ESI, pos. ) m / z: 413.1 (M + 1). 62 (E) -1 - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -ethanone The title compound was prepared from 2-acetylphenyl boronic acid (0.0005 mol, 0.082 g) and Compound 13d (0.00025 mol, 0.096 g) to provide the product as a bright yellow solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.75-7.91 (m, 5 H) 7.55-7.68 (m, 4 H) 7.41-7.47 (m, 3 H) 2.46 (s, 3 H) MS (ESI, ion pos.) m / z: 425.1 (M + 1). 63 (E) -2-. { 6-Fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide The title compound was prepared from 2-aminocarbonyl phenylboronic acid (0.0005 mol, 0.083 g) and Compound 13d (0.00025 mol, 0.096 g) to provide the product as a sticky cinnamon solid. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 7.93 (d, 2 H, J = 8.6 Hz) 7.83 (d, 2 H, J = 8.6 Hz) 7.40-7.71 (m, 8H) MS (ESI, pos. Ion) m / z: 426.0 (M + 1). 64 (E) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -acetamide The The title compound was prepared from 2-acetamidophenyl boronic acid (0.0005 mol, 0.089 g) and Compound 13d (0.00025 mol, 0.096 g) to provide the product as a white solid. 1 H NMR (400 MHz, DMSO-d 6) d (ppm): 8.68 (s, 1 H) 8.03 (s, 1 H) 7.80-7.96 (m, 6H) 7.35-7.50 (m, 3H) 7.20 (d, 2H, J = 4.1 Hz) 1.8 (s, 3H) MS (ESI, pos. Ion) m / z: 440.1 (M + 1).
Comp. Name and data 65 (E) -N- (2- {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) methanesulfonamide The title compound was prepared from 2-methylsulfonylaminophenyl boronic acid (0.0005 mol, 0.108 g) and Compound 13d (0.00025 mol, 0.096 g) to afford the product as a white solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.65 (s, 1 H) 7.59 (d, 1 H, J = 6.7 Hz) 7.26-7.48 (m, 10 H) 2.95 (s, 3 H) MS ( ESI, pos. Ion) m / z: 476.1 (M + 1).
EXAMPLE 14 (E) - (2 6-chloro-2-r2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazole-5-yl ^ phenyl-methanol (Comp.66) Step A.
N- (4-bromo-5-chloro-2-nitro-phenyl) -2,2,2-trifluoroacetamide 4-bromo-3-chloromethyl aniline (4.1 g, 0.02) was added in portions moles) to a solution of stirred and cooled ice trifluoroacetic anhydride (50 mi) To the resulting solution was added KN03 (2.22 g, 0.022 moles, 1.1 eq) in portions. The reaction mixture was stirred at 0 ° C for 1 hour and then left to warm to room temperature throughout the night. The mixture of The reaction was diluted with ice water (150 ml) and the solid was collected by vacuum filtration. The solid was washed with water (50 ml) and dried in vacuo to provide the title compound 14a as a pale yellow solid (5.55) 9) - Step B 4-bromo-5-chloro-2-nitro-phenylamine Compound 14a (5.2 g, 0.015 mol) was dissolved in a mixture of methanol (25 ml) and saturated aqueous solution of K2CO3 (15 ml). The reaction mixture was stirred at room temperature for 10 hours. The reaction mixture was diluted with water (25 ml) and the product was collected by vacuum filtration to provide the title compound 14b as a yellow solid (2.71 g). 1 H-NMR (400 MHz, CDCl 3) d (ppm): 8.39 (s, 1 H) 6.98 (s, 1 H) 6. 08 (bs, 2H). MS (ESI, pos. Ion) m / z: 250.9 (Br, Cl pattern).
Step C 4-Bromo-5-chloro-benzene-1,2-diamine Compound 14b (2.0 g, 0.008 mol) was dissolved in 20 ml of ethanol. Zinc powder (4.7 g, 0.072 mole) was added in portions followed by the addition of ammonium chloride (0.88 g, 0.016 mole, 2 eq). The reaction mixture was stirred at room temperature overnight (16 hours). The reaction mixture was filtered on a pad of celite and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate (30 ml) and washed with 25 ml of brine. The organic fractions were dried with Na 2 SO 4, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2: MeOH, 96: 4-94: 6) to give the title compound 14c as a dark yellowish-brown solid (1.08 g) and used immediately in the next reaction . MS (ESI, pos. Ion) m / z: 220.9 (Br pattern, Cl).
Step D (E) -5-bromo-6-chloro-2- [2- (4-trifluoromethyl-phenyl) -vinin-1 H-benzimidazole 4-trifluoromethyl cinnamic acid (1.2 g, 0.0055, 1.1 eq) was dissolved in 30 ml of POCI3. To this solution was added Compound 14c (1.08 g, 0.005 mole), and the reaction mixture was heated to reflux for 6 hours (The reaction mixture was quite dark). The reaction mixture was cooled to room temperature and then evaporated in vacuo. The residue was taken up in 50 ml of ethyl acetate and washed with 50 ml of brine. The organic fractions were dried with Na 2 SO 4 > filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography (silica gel hexanes: EtOAc, 3: 1-3: 2) to give the title compound 14d as a light brown solid (0.80 g). 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 7.57-8.21 (m, 4 H) 7.35 (d, 1 H, J = 19 Hz) 6.72 (d, 1 H, J = 18.5 Hz). MS (ESI, pos. Ion) m / z: 401.0.
Step E (B- (2- (6-Chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -methanol Compound 14d (0.00025 moles, 0.100 g) was dissolved in 5 ml of dioxane, 2-hydroxymethyl phenylboronic acid (0.0005 mole, 0.067 g, 2.0 equiv) was added followed by aqueous Na2CO3 (0.00055 mole, 0.28 ml of 2M solution) and dichlorobis (tricyclohexylphosphino) -palladium (II) ( 0.01 g, 6% in moles). The reaction mixture was heated in a microwave at 110 ° C for 20 minutes. The reaction mixture was cooled and the solvent was evaporated in vacuo. The residue was taken in 10 ml of CH2Cl2, and washed successively with 10 ml of saturated aqueous NaHCOa and 10 ml of brine. The organic fractions were dried with a2SO4, filtered and the solvent was evaporated in vacuo. The residue was purified by chromatography (silica gel, CH2Cl2: MeOH, 98: 2-95: 5) to give the title compound 66 as a sticky yellow solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.82-7.85 (d, 2 H, J = 8.4 Hz) 7.72-7.74 (d, 2 H, J = 8.3 Hz) 7.56-7.66 (m, 3 H) 7.26- 7.43 (m, 5H) 5.05 (s, 1 H) 4.58 (s, 2H). MS (ESI, pos. Ion) m / z: 395.3 (-CH2OH). By the procedures described in Example 14 and reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 67 (£) -1 - (2- {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v] n-1] -1 H -benzimidazole-5 -yl.}.-phenyl] -ethanone The title compound was prepared from 2-acetylphenyl boronic acid (0.0005 mol, 0.082 g) and Compound 14d (0.00025 mol, 0. 00 g) to provide the product as a pale yellow solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.80-7.84 (m, 2 H) 7.70-7.74 (m, 2 H) 7.67 (s, 1 H), 7.50-7.64 (m, 2 H) 7.27-7.43 ( m, 5H), 1.36 (s, 9H). MS (ESI, pos. Ion) m / z: 441.1 (M + 1). 68 (E) -2-. { 6-chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenol The title compound was prepared from 2-hydroxyphenyl boronic acid (0.0005 mol, 0.108 g) and Compound 14d (0.00025 mol, 0.069 g) to afford the product as a dark yellow solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 6.2-6.6 (m, 5H) 5.99- 6.05 (m, 5H) 5.59-5.66 (2H) 7.80-7.84 (m, 2H). MS (ESI, pos. Ion) m / z: 415.0 (M + 1).
EXAMPLE 15 (E) -2- 2-r2- (4-trifluoromethyl-phenyl -vinin-1H-benzimidazol-5-illbenzenesulfonamide (Compound 70) (a-N-tert-butyl-2- {2-r2- (4-trifluoromethyl-phenyl) -vinin-1 H-benzimidazol-5-yl) -benzenesulfonamide (Compound 309) Step A (aN-tert-butyl-2- (2-r2- (4-trifluoromethyl-phenyl) -vinyl-1H-benzimidazol-5-yl> -benzenesulfonamide A mixture of 2- (t-butylamino) sulfonylphenyl acid boronic (12.4 g, 0.048 moles), Compound 10c (13.6 g, 0.037 moles), Pd (dppf) CI2CH2CI2 (3.00 g, 3.70 mmol), TBAB (1.9 g, 0.037 mmol) and Na2CO3 (31.4, 0.296 moles) in 750 ml of the mixed solvent (DME: water, 4: 1) was heated at 90 ° C for 12 hours. The reaction mixture was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 1: 1) to give the title compound 309 as a yellow oil. H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.84 (d, 2H, J = 8.4 Hz) 7.73 (d, 2H, J = 8.4 Hz) 7.70-7.62 (m, 4H) 7.54 (dt, 1 H, J = 1.6 and 8.6 Hz) 7.41 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.37-7.31 (m, 2H) 1.00 (s, 9H) MS (ESI, pos. Ion) m / z: 490.3 (M + 1).
Step B (a-2- (2- [2- (4-trifluoromethyl-phenyl) -vinyl-1-H-benzimidazol-5-yl) -benzenesulfonamide A solution of Compound 309 in 60 ml of TFA was heated to 70 ° C. The reaction was concentrated, the residue was dissolved in EtOAc, and washed with saturated NaHCO 3 solution, The organic phase was dried with Na 2 SO 4, filtered, and the residue was concentrated, The residue was purified by chromatography ( silica, hexanes: EtOAc, 1: 2) to give the title compound 70 as a dark brown solid, MP 168-170 ° C. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.16 (dd, 1 H , J = 1.2 and 8.0 Hz) 7.95-7.91 (m, 3H) 7.82-7.76 (m, 4H) 7.70-7.56 (m, 3H) 7.44 (s, 1 H) 7.16 4 (d, 1 H, J = 9.6 Hz) MS (ESI, pos. Ion) m / z: 444.3 (M + 1).
Through the procedures described in Example 15 and reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention: Comp. Name and data 71 (E) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -1 H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 8.10 (d, 2H, J = 8.4 Hz) 8.01 (d, 2H, J = 8.4 Hz) 7.71-7.53 (m, 5H) 7.44 (d, 1 H, J = 16.4 Hz) 7.41 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.35 (dd, 1 H, J = 1.2 and 8.4 Hz) MS (ESI, pos. Ion) m / z: 508.3 (M + 1). 398 (£) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide The title compound was prepared from 2-N, N-dimethylaminosulfonylphenyl boronic acid and Compound 10c. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.08 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.84 (d, 2 H, J = 8.4 Hz) 7.73 (d, 2 H, J = 8.8 Hz) 7.69-7.56 (m, 5H) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.33 (d, 1 H, J = 16.4 Hz) 7.28 (dd, 1 H, J = 1.6 and 8.4 Hz) 2.34 ( s, 6H) MS (ESI, pos. ion) m / z: 472.5 (M + 1). 441 (E) -4-fluoro-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide The title compound was prepared from 2-tert-butylaminosulfonyl-5-fluorophenylboronic acid and Compound 10c. H-NMR (400 MHz, CD3OD) d (ppm): 8.18 (dd, J = 5.6, 8 Hz, 1 H), 7.94 (d, J = 5.6, 8 Hz, 1 H), 7.84 (d, J = 8 Hz, 2H), 7.73 (s, 1 H), 7.71-7.69 (m, 2H), 7.63 (d, J = 8 Hz, 1 H), 7.35-7.32 (m, 1 H), 7.28-7.22 ( m, 2H), 7.14 (dd, J = 2, 9 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H15F4N302S: 462.4 (M + H), Experimental 462.2.
Comp. Name and data 444 (E) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl} - benzenesulfonamide The title compound was prepared from 2-tert-butylaminosulfonyl-5-trifluoromethylphenyl boronic acid and Compound 10c. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.33 (d, J = 8 Hz, 1 H), 7.88 (s, 1 H), 7.85 (d, J = 8 Hz, 2 H), 7.74- 7.68. (m, 6H), 7.36-7.32 (m, 1 H), 7.34 (d, J = 16.4 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H15F6N302S: 512.5 (M + H), Experimental 512.3. 446 (E) -5-trifluoromethyl-2-. { 2- [2- (4- Trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide The title compound was prepared from 2-tert-butylaminosulfonyl-4-trifluoromethylphenyl boronic acid and Compound 10c. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.42 (s, 1 H), 7.94 (d, J = 8 Hz, 1 H), 7.85 (d, J = 8 Hz, 2 H), 7.73 (d, J = 8 Hz, 2H), 7.71 (d, J = 8 Hz, 2H), 7.64 (d, J = 8 Hz, 2H), 7.34 (d, J = 16.4 Hz, 2H). Mass spectrum (LCMS, ESI pos.) Calculated for 512.1 (M + H), Experimental 512.2.
EXAMPLE 16 (E) -2- 2-r 2 - (4-trifluoromethoxy-phenyl) -vinn-1 H -benz »midazol-5-yl > - benzenesulfonamide (Compound 69) Step A. tert-butyl ester of (5-bromo-2-tert-butoxycarbonylamino-pheni-carbamic acid) 4-bromo-phenylenediamine (25 g, 0.134) was added in portions moles) to di-t-butyl bicarbonate (175 g, 0.802 moles) at 25 ° C, and the mixture of reaction was stirred for 10 hours. The mixture was purified by chromatography (silica gel, hexanes to hexanes: EtOAc, 1: 1) to give the title compound 16a as a light brown solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 7.76 (brs, 1 H) 7.32 (brs, 1 H) 7.22 (dd, 1 H, J = 2.0 and 8.8 Hz) 6.72 (brs, 1 H) 6.53 (brs, 1 H).
Step B tert-butyl ester of (3-tert-butoxycarbonylamino-2'-tert-butylsulfamoyl-biphenyl-4-yl) -carbamic acid A mixture of 2- (t-butylamino) sulfonylphenyl boronic acid (4.7 g, 0. 018 mmole), Compound 16a (4.7 g, 0.012 mmole), Pd (dppf) CI2-CH2Cl2 (0.99 g, 0.0012 mmole), TBAB (3.90 g, 0.012 mmole), and 20 ml of Na2CO3 (ac) 1 M in 100 My DME was heated to 100 ° C for 12 hours. The reaction mixture was concentrated, and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 2: 1) to give the title compound 16b as a yellow oil.
Step C 3 ', 4'-diamino-biphenyl-2-sulfonic acid tert-butylamide A mixture of Compound 16b in 20 ml of 4M HCl in dioxane was stirred for 3 hours. The reaction mixture was concentrated, diluted with EtOAc and washed with saturated NaHCO3 (aq), then dried with Na2SO4 and filtered. The filtrate was concentrated to provide the title compound 16c as a brown oil. H-NMR (400 MHz, CD3OD) d (ppm): 8.04 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.56 (dt, 1 H, J = 1.2 and 8.2 Hz) 7.44 (dt, 1 H, J = 1.2 and 8.4 Hz) 7.33 (dd, 1 H, J = 1.2 and 7.6 Hz) 6.86 (d, 1 H, J = 1.6 Hz) 6.77 (d, 1 H, J = 7.6 Hz) 6.73 (dd, 1 H , J = 2.0 and 8.0 Hz) 0.97 (s, 9H). MS (ESI, pos. Ion) m / z. 319.9 (M + 1).
Step D (E) -2-. { 2-r 2 - (4-trifluoromethoxy-phenyl) -vinyl-1 H-benzimidazol-5-yl) -benzenesulfonamide A mixture of Compound 16c (0.120 g, 0.376 mmol), trans 4- (trifluoromethoxy) -cinnamic acid (0.105 g) , 0.451 mmole), and 0.4 ml of 4N HCl (ac) in 4 ml of ethylene glycol was heated at 180 ° C for 1 hour. The reaction mixture was purified directly by HPLC (YMC ODS-A, H2O: MeCN, 90:10 to 40:60, for 10 min) to give the title compound 69 as a white solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.75 (d, 2 H, J = 8.4 Hz) 7.68-7.53 (m, 5 H) 7.41 (dd) , 1 H, J = 1.2 and 7.6 Hz) 7.37-7.33 (m, 3H) 7.19 (d, 1 H, J = 16.8 Hz) MS (ESI, pos. Ion) m / z: 460.3 (M + 1). Through the procedures described in Example 16 and reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention: Comp. Name and data 79 (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (cid, 1 H, J = 1.2 and 7.6 Hz) 7.68-7.54 (m, 7H) 7.46-7.40 (m, 3H) 7.38 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.19 (d, 1 H, J = 16.8 Hz) MS (ESI, pos. Ion) m / z: 410.4 (M + 1). 85 (£ -2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm ): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.99 (d, 2H, J = 8.4 Hz) 7.89 (d, 2H, J = 8.4 Hz) 7.71 -7.53 (m, 5H) 7.41 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.36 (d, 1 H, J = 16.4 Hz) 7.34 (dd, 1 H, J = 1.6 and 8.4 Hz) MS (ESI, pos. Ion) m / z: 453.4 ( M + 1) .357 (£) -2- { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -benzenesulfonamide 1H-NMR (400 MHz , CD3OD) d (ppm): 8.13 (d, 1 H, J = 8.0 Hz) 7.83-7.75 (m, 2H) 7.67-7.53 (m, 4H) 7.38 (t, 2H, J = 9.2 Hz) 7.22 (d , 1 H, J = 16.8 Hz) 7.08-7.03 (m, 2H) MS (ESI, pos. Ion) m / z: AMA (M + 1) .358 (E) -2- { 2- [2 - (3,4-difluoro-phenyl) -vinyl] -H-benzimidazol-5-yl.} - benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.72-7.55 (m, 6H) 7.48-7.35 (m, 4H) 7.20 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. Ion) m / z: AMA (M + 1). (E) -2- { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1H-benzimidazole-5 -il} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.84 (d, 1 H, J = 16.8 Hz) 7.70-7.54 (m, 5H) 7.41 (dd, 2H, J = 1.6 and 8.4 Hz) 7.33 (d, 1 H, J = 16.8 Hz) 7.29-7.23 (m, 2H) MS (ESI, pos. Ion) m / z AMA (M + 1) . 360 (£.}. -2- { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.81 (d, 1 H, J = 16.8 Hz) 7.69-7.54 (m, 5H) 7.46-7.38 (m, 2H) 7.33 (d , 1 H, J = 16.8 Hz) 7.26-7.14 (m, 2H) MS (ESI, pos. Ion) m / z: AMA (M + 1).
Comp. Name and data 361 (E) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - 1H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.71-7 55 (m, 5H) 7.42 (td, 2H, J = 1.4 and 8.4 Hz) 7.34-7.28 (m, 3H) 7.04-6.99 (m, 1 H) MS (ESI, pos. Ion) m / z: 412.4 (M + 1). 362 (E) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzyldazole-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.37-7.51 (m, 8H) 7.41 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.35 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.29 (d, 1 H, J = 8.8 Hz) 7.25 (d, 1 H, J = 16.8 Hz) 7.34 (dd, 1 H, J = 1.6 and 8.4 Hz) MS (ESI, pos. ion) m / z: 460.4 (M + 1). 363 (E) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8. 13 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.93 (d, 1 H, J = 1.2 and 7.6 Hz) 7.65-7.47 (m, 6H) 7.42-7.29 (m, 4H) 7.22 (d, 1 H , J = 16.8 Hz) MS (ESI, pos. Ion) m / z. 454.3 (M + 1). 364 (E) -2-. { 2- [2- (2-trifluoromethyl] -phenyl) -vinyl] -1 H-benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8. 14 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.10 (dd, 1 H, J = 2.0 and 16.4 Hz) 8.01 (d, 1 H, J = 7.6 Hz) 7.80 (d, 1 H, J = 7.6 Hz) 7.75-7.55 (m, 6H) 7.42 (dd, 2H, J = 1.2 and 8.4 Hz) 7.25 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. Ion) m / z: 444.3 (M +1) 365 (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.16 (d, 1 H, J = 7.6 Hz) 8.13 (s, 1 H) 7.90 (d, 1 H, J = 9.2 Hz) 7.68 (d, 1 H, J = 14.4 Hz) 7.65-7.49 (m, 4H) 7.43-7.38 (m, 4H) 7.25 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. ion) m / z : 410.3 (M + 1). 366 (E) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -H-benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.35 (d, 1 H, J = 16.4 Hz) 8.16 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.97 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.84 (s, 1 H) 7.80 (d, 1 H, J = 9.2 Hz) 7.76 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.70-7.60 (m, 3H) 7.52 (dt , 1 H, J = 1.2 and 8.2 Hz) 7.45-7.39 (m, 2H) 7.32 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. Ion) m / z: 454.3 (M + 1).
Comp. Name and data 367 (£) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8. 15 (dd, 1 H, J = 1.2 and 7.6 Hz) 8.12-8.08 (m, 2H) 7.76- 7.41 (m, 8H) 7.25 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. Ion) m / z: 461.4 (M + 1). 368 (£) -2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 8.10 (t, 1 H, 7.0 Hz) 7.91 (d, 1 H, J = 16.4 Hz) 7.75-7.54 (m, 5H) 7.46-7.34 (m, 4H) MS (ESI, pos. Ion) m / z: 461.4 (M + 1). 369 (E) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8. 16 (dd, 1 H, J = 1.6 and 8.0 Hz) 8.12-8.10 (m, 2H) 7.94 (d, 1 H, J = 16.8 Hz) 7.85 (dd, 1 H, J = 0.8 and 1.6 Hz) 7.80 ( dd, 1 H, J = 0.8 and 8.8 Hz) 7.70-7.59 (m, 3H) 7.52 (t, 1 H, J = 9.8 Hz) 7.43 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.39 (d, 1 H, J = 16.8 Hz) MS (ESI, pos. Ion) m / z: 462.3 (M + 1). 370 (E) -2-. { 2- [2- (2,3,4-trifluoro-phenyl) -vinyl] -H-benzimidazole-5-yl} -benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.14 (d, 1 H, J = 8.0 Hz) 7.79 (d, 1 H, J = 16.8 Hz) 7.68 (d, 1 H, J = 16.0 Hz) 7.64-7.55 (m, 4H) 7.43-7.40 (m, 2H) 7.31 (d, 1 H, J = 16.8 Hz) 7.23 (q, 1 H, J = 8.1 Hz) MS (ESI, ion pos .) m / z: 430.4 (M + 1). 371 (E) -2-. { 2- [2- (2,4,5-trifluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.84-7.79 (m, 1 H) 7.75 (d, 1 H, J = 15.6 Hz) 7.68-7.53 (m, 4H) 7.41 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.37 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.33-7.25 (m, 2H) MS (ESI , ion pos.) m / z: 430.3 (M + 1). 372 (£) -2-. { 2- [2- (2,6-difluoro-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 0.8 and 7.6 Hz) 7.85 (d, 1 H, J = 16.8 Hz) 7.70-7.54 (m, 4H) 7.49 (d, 1 H, J = 16.8 Hz) 7.46-7.40 (m, 3H) 7.10 (t, 2H, J = 8.8 Hz) MS (ESI, pos. Ion) m / z: 412.3 (M + 1).
Comp. Name and data 373 (£) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.25 (s, 2H) 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.95 (s, 1 H) 7.71 (d, 1 H, J = 16.8 Hz) 7.68-7.53 (m, 4H) 7.44 (d, 1 H, J = 16.8 Hz) 7.42 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.35 (dd, 1 H, J = 1.6 and 8.0 Hz) MS (ESI, pos. Ion) m / z: 512.4 (M + 1). 374 (£) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl] -vinyl] -1 H -benzyldazol-5-yl} -1 H-NMR (400 MHz, CD3OD) d (ppm): 8.36 (s, 1 H) 8.24 (dd, 1 H, J = 2.0 and 16.4 Hz) 8.16 (dd, 1 H, J = 1.2 and 8.0 Hz ) 8.06 (d, 1 H, J = 8.4 Hz) 7.84 (d, 1 H, J = 8.4 Hz) 7.83 (s, 1 H) 7.79 (d, 1 H, J = 8.8 Hz) 7.69- 7.57 (m, 3H) 7.48-7.42 (m, 2H) MS (ESI, pos. Ion) m / z: 512.4 (M + 1). 375 (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -v-n-1] -1H-benzyldazole-5-yl} 1 H-NMR (400 MHz, CD3OD) d (ppm): 8.51 (d, 1 H, J = 16.0 Hz) 8.16-8.10 (m, 2H) 8.03 (d, 1 H, J = 8.4 Hz) 7.82 ( dd, 1 H, J = 1.6 and 8.0 Hz) 7.75-7.55 (m, 4H) 7.49-7.36 (m, 2H) 7.28 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. ion) m / z: 488.1 (M + 1). 376 (E) -2-. { 2- [2- (3-Bromo-phenyl) -vinyl] -1H-benzimidazol-5-yl} 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.15 (d, 1 H, J = 7.6 Hz) 7.89 (s, 1 H) 7.74-7.58 (m, 7H) 7.48-7.37 (m, 3H ) 7.27 (d, 1 H, J = 16.4 Hz) MS (ESI, pos. Ion) m / z: 454.3 (M). 378 (£) -2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -vinyl] -H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8. 14 (dd, 1 H, J = 1.6 and 8.0 Hz) 8.04 (d, 1 H, J = 2.0 Hz) 7.93 (dd, 1 H, J = 2.0 and 8.4 Hz) 7.71 -7.54 (m, 6H) 7.43- 7.38 (m, 2H) 7.32 (d, 1 H, J = 16.8 Hz) MS (ESI, pos. Ion) m / z: 478.4 (M + 1). 379 (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8. 15 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.00 (dd, 1 H, J = 2.4 and 6.4 Hz) 7.88 (d, 1 H, J = 16.4 Hz) 7.76-7.57 (m, 5H) 7.51 ( dd, 1 H, J = 1.6 and 8.8 Hz) 7.42 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.38 (d, 1 H, J = 16.4 Hz) 7.20 (dd, 1 H, J = 8.8 and 10.4 Hz) MS (ESI, pos. Ion) m / z: 472.3 (M + 1).
Comp. Name and data 423 (£) -2-. { 2- [2- (3-fluoro-4-trifluoromethy1-pheny1) -vin1] -1H-benzyldazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, J = 1.2, 8.2 Hz, 1 H), 7.74-7.62 (m, 7H), 7.43-7.34 (m, 3H), 6.64 (d, J = 16.0 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H15F N3O2S: 462.1 (M + H), Experimental 462.2. 424 (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm):. 8.13 (dd, J = 1.6, 8.0 Hz, 1 H), 7.99 (t, J = 7.2 Hz, 1H), 7.83 (d, J = 16.8 Hz, 1H), 7.67-7.52 (m, 4H), 7.45 ( s, 1H), 7.43- 7.40 (m, 3H), 7.34 (dd, J = 1.6, 7.6 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H 5F N302S: 462.1 (M + H), Experimental 462.2. 425 (£) -2-. { 2- [2- (3-ethoxy-phenyl) -v] nyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8.0 Hz, 1 H), 7.99 (t, J = 7.2 Hz, 1H), 7.57 (d, J = 16 Hz, 1 H), 7.67-7.60 (m, 2H), 7.45 (s, 1 H), 7.43- 7.40 (m, 2H), 7.25 (t, J = 4 Hz, 1 H), 7.11 (d, J = 8 Hz, 1 H), 7.07-7.08 (m, 1 H), 6.92-6.89 (m, 1 H), 6.45 (d, J = 16 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H21 N3O3S: 420.1 (M + H), Experimental 420.2. 426 (£) -2- (2-Stryl-1 H-benzimidazol-5-yl) -benzenesulfonamide 1 H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 7.8 Hz , 1 H), 7.66-7.58 (m, 6H), 7.54 (dt, J = 1.6, 7.6 Hz, 1 H), 7.44-7.40 (m, 3H), 7.38-7.34 (m, 1 H), 7.31 ( dd, J = 1.6, 8 Hz, 1 H), 7.18 (d, J = 16.4 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH17N302S: 376.1 (M + H), Experimental 376.3. 427 (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.82 (s, 1 H), 7.65-7.61 (m, 3H), 7.60- 7.54 (m, 3H), 7.52 (s, 1 H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.32 (dd, J = 1.6, 8 Hz, 1 H), 7.22 (d, J = 16.4 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for 444.0 (M + H), Experimental 444.1.
Comp. Name and data 428 (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H-benzimidazole-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.78 (d, J = 8 Hz, 1 H), 7.75 (d, J = 8 Hz, 1 H), 7.72 (s, 1 H), 7.55-7.54 (m, 1 H), 7.62 (dd, J = 1.6, 8 Hz, 1 H), 7.54 (dt, J = 1.6, 8 Hz , 1 H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.34-7.26 (m, 4H). Mass spectrum (LCMS, ESI pos.) Calculated for C21H15CIFN302S: 428.9 (M + H), Experimental 430.2. (£) -2-. { 2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzamdazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.65-7.60 (m, 4H), 7.58-7.52 (m, 3H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.32-7.29 (m, 3H), 7.13 (d, J = 16.8 Hz, 1 H), 2.94 (h, J = 2.4 Hz, 1 H), 1.27 (d, J = 8 Hz, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H23N3O2S: 418.1 (M + H), Experimental 418.4. 430 (£) -2- [2- (2-p-tolyl-vinyl) -1H-benzimidazol-5-yl] -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.65-7.58 (m, 5H), 7.53 (d, J = 7.6 Hz, 2H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.30 (dd, J = 1.6, 8 Hz, 1 H), 7.23 (d, J = 8 Hz, 2 H), 7.1 1 (d, J = 16.8 Hz, 1 H), 2.36 (s, 3 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H19N302S: 390.1 (M + H), Experimental 390.5. (£) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl-J-1 H-benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.80 (d, J = 16 Hz, 1 H), 7.73 (t, J = 7.2 Hz, 1 H), 7.66-7.60 (m, 4H), 7.57-7.52 (m, 1 H), 7.51-7.46 (m, 1 H), 7.42 (dd, J = 1.6, 8 Hz, 1 H) , 7.33 (dd, J = 1.6, 8 Hz, 1 H), 7.22 (d, J = 16.8 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C21H15CIFN302S: 428.9 (M + H), Experimental 428.3. (£) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl] -vinyl] -1 H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.80 (dd, J = 2, 7.2 Hz, 1 H), 7.65-7.52 ( m, 6H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.33-7.28 (m, 2H), 7.16 (d, J = 16.8 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C21Hl5CIFN302S: 428.9 (M + H), Experimental 428.3.
Comp. Name and data 433 (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide 1 H-NMR (400 MHz, CD3OD) d (ppm ): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 8.01 (s, 1 H), 7.91-7.82 (m, 4H), 7.80 (d, J = 16.8 Hz, 1 H), 7.66-7.59 (m, 3H), 7.55 (dd, J = 1.6, 8 Hz, 1 H), 7.52-7.48 (m, 2H), 7.42 (dd, J = 2, 7.6 Hz, 1 H), 7.32 (dd, J = 1.6, 8 Hz, 1 H), 7.30 (d, J = 16.8 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C25H19N302S: 426.5 (M + H), Experimental 426.3. 434 (£) -2-. { 2- [2- (4-fluoro-phenyl) -v] nyl] -1H-benzimidazole-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.69-7.66 (m, 2H), 7.65-7.52 (m, 5H) , 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.31 (dd, J = 1.6, 8 Hz, 1 H), 7.18-7.10 (m, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH16FN302S: 394.4 (M + H), Experimental 394.3. 435 (E) -2-. { 2- [2- (4-difluoromethyl-phenyl) -vinyl] -1 H-benzimidazole-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.70 (d, J = 8 Hz, 2H), 7.66- 7.61 (m, 4H), 7.54 (dt, J = 1.6, 8 Hz, 1 H), 7.42 (dd, J = 1.6, 8 Hz, 1 H), 7.32 (d, J = 8 Hz, 1 H), 7.20 (d, J = 8 Hz, 2H), 7.15 (d, J = 16 Hz, 1 H), 6.89 (s, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H17F2N302S: 426.5 (M + H), Experimental 426.3. 436 (£) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1H), 7.78 (s, 1 H), 7.73 (dd, J = 1.6, 8 Hz, 1 H), 7.66-7.61 (m, 4H), 7.54 (dt, J = 1.6, 8 Hz, 1 H), 7.44 (d, J = 8 Hz, 1 H), 7.41 (dd, J = 1.6, 8 Hz , 1 H), 7.33 (d, J = 8 Hz, 1 H), 7.34 (d, J = 16 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H15F4N302S: 461.4 (M + H), Experimental 462.2. 437 (£) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.97 (d, J = 16.8 Hz, 1 H), 7.84 (d, J) = 8 Hz, 1 H), 7.66-7.51 (m, 5H), 7.41-7.37 (m, 2H), 7.32 (d, J = 1.6, 8 Hz, 1 H), 7.20 (d, J = 16 Hz, 1 HOUR). Mass spectrum (LCMS, ESI pos.) Calculated for C21H15CI2N302S: 445.3 (M + H), Experimental 446.1. 2 4 Comp. Name and data 438 (E) -2-. { 2- [2- (2-Chloro-6-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide 1H-RN (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.89 (d, J = 16.8 Hz, 1 H), 7.66-7.60 (m , 3H), 7.54 (dt, J = 1.6, 8 Hz, 1 H), 7.45 (d, J = 16 Hz, 1 H), 7.43 (s, 1 H), 7.41 -7.32 (m, 3H), 7.24 -7.18 (m, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH15CIFN302S: 428.9 (M + H), Experimental 428.3. 439 (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.94 (dd, J = 1.6, 8 Hz, 1 H), 7.68-7.62 ( m, 6H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.32 (d, J = 1.6, 8 Hz, 1 H), 7.28 (t, J = 8 Hz, 1 H), 7.16 ( d, J = 16.8 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C21H15BrFN302S: 473.3 (M + H), Experimental 473.2. 440 (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.13 (dd, J = 1.6, 8 Hz, 1 H), 7.94 (dd, J = 1.6, 8 Hz, 1 H), 7.68-7.62 ( m, 6H), 7.41 (dd, J = 1.6, 8 Hz, 1 H), 7.32 (d, J = 1.6, 8 Hz, 1 H), 7.28 (t, J = 8 Hz, 1 H), 7.16 ( d, J = 16.8 Hz, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C21H15BrFN302S: 473.3 (M + H), Experimental 473.2.
PROPHETIC EXAMPLE 17 Through the procedures described in Example 15 or 16 and reagents, starting materials and conditions known to the experts in the art, the following representative prophetic compounds can be prepared of the present invention: Comp. Name and data (E) -2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -2- (2- {2- [4- (2,2,2-trifluoro-ethoxy) -phenyl} -vinyl} - 1 H-benzimidazol-5-yl) -benzenesulfonamide, (£) -2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phen 1-vinyl) -1H-benzyldazol-5-yl) -benzenesulfonamide, (£) -2-. { 2- [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-trifluoromethyl-pheny] -vinyl] -1 H-benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-methanesulfonylamine-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide and (£) -2-. { 2- [2- (4-trifluoromethanesulfonyllamino-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide.
EXAMPLE 18 (a-N-Methyl-2 2-f2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazol-5-ylV Benzenesulfonamide (Comp 310) Step A N-methylbenzenesulfonamide acid -2-boronic acid To a solution of N-methylbenzenesulfonamide (2.00 g, 0.0117 mmoles) in 20 ml of THF at 0 ° C was added dropwise n-butyl lithium (1.6 M in hexanes, 14.6 ml, 0.0234 mmoles). After 30 min, triisopropyl borate (3.1 ml, 0.0164 mmol) was added and the mixture was stirred at 0 ° C for 2 hours. hours. The reaction is quenched by the addition of 20 ml of 1M HCl (ac). The mixture was extracted with EtOAc, and the organic fractions were washed with brine, dried with a2SO4, filtered and the filtrate was concentrated to give the title compound 18a as a yellow oil. H-NMR (400 MHz, CD3OD) d (ppm): 7.81 (d, 1 H) 7.62-7.56 (m, 2H) 2.52 (s, 3H).
Step B tert-butyl ester of (3-tert-butoxycarbonylamino-2'-methylsulfamoyl-biphenyl-4-yl) -carbamic acid A mixture of the freshly prepared Compound 18a (9.3 g, 0.0434 mole), Compound 16a (1 1.2 g, 0.289 mole) ), Pd (dppf) CI2CH2Cl2 (4.7 g, 6.42 mmol), TBAB (9.3 g, 0.0289 mol), in 120 ml of 1 M Na2CO3 (ac) and 600 ml DME was heated at 85 ° C for 10 hours. The reaction mixture was cooled and concentrated. The residue was purified by chromatography (silica gel, hexanes: EtOAc, 2: 1) to give the title compound 18b as a yellow oil. 1 H NMR (400 MHz, CDCl 3) d (ppm): 8.12 (d, 1 H) 7.86 (d, 1 H) 7.62-7.46 (m, 3 H) 7.22 (d, 1 H) 7.14 (d, 1 H) 2.62 (d, 3H) 1.55 (s, 9H) 1.44 (s, 9H).
Step C 3 ', 4'-diamino-biphenyl-2-sulfonic acid methylamide A solution of Compound 18b (21.4 g, 0.0995 mol) in 210 ml of 4M HCl in dioxane was stirred for 4 hours. The reaction mixture was concentrated, made basic with 1 M NaOH (aq) and extracted with EtOAc. The organic fraction was dried with Na 2 SO 4, filtered and the filtrate was concentrated to provide the title compound 18c as a brown oil. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.00 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.59 (dt, 1 H, J = 1.6 and 8.4 Hz) 7.48 (dt, 1 H, J = 1.2 and 8.4 Hz) 7.33 (dd, 1 H, J = 1.2 and 8.0 Hz) 6.79 (d, 1 H, J = 2.0 Hz) 6.75 (d, 1 H, J = 8.4 Hz) 6.68 (d, 1 H , J = 2.0 and 7.6 Hz) 2.93 (s, 3H) MS (ESI, pos. Ion) m / z: 277.9 (M + 1).
Step D (E) -N-methyl-2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -benzenesulfonamide A mixture of Compound 18c (0.100 g, 0.361 mmol) and 4-trifluoromethyl cinnamic acid (0.324) mmoles) in 2 ml of POCI3 was heated at 100 ° C for 14 hours. Evaporation of the reaction mixture afforded a residue which was then purified by HPLC (H20: MeCN, 90: 10 to 30:70, for 15 min) to give the title compound 310 as a white solid. 1 H-NMR (400 MHz, CD3OD) d (ppm): 8.07 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.85 (d, 2H, J = 8.4 Hz) 7.73 (d, 2H, J = 8 Hz) 7.69-7.63 (m, 3H) 7.58 (dt, 2H, J = 1 .6 and 7.2 Hz) 7.44 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.34 (d, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 499.2 (M + MeCN + 1).
Through the procedures described in Example 18 and reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention: Comp. Name and data 312 (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.68-7.60 (m, 3H) 7.59-7.55 (m, 6H) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.30 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.21 (d, 1 H, J = 16.4 Hz) 2.38 (s, 3H) MS (ESI, ion pos.) m / z: 509.2 (M + MeCN). 314 (E) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1H-benzimidazol-5-yl] -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.04 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.77 (d, 1 H, J = 16.4 Hz) 7.70 (d, 1 H, J = 15.2 Hz) 7.66-7.64 (m, 2H) 7.61-7.55 (m , 3H) 7.46 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.41 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.26 (d, 2H, J = 7.6 Hz) 7.15 (d, 1 H, J = 16.8 Hz) 2.42 (s, 3H) 2.36 (s, 3H) MS (ESI, pos. Ion) m / z: 404.2 (M + 1). 315 (E) -2-. { 2- [2- (4-Fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.82-7.73 (m, 4H) 7.70-7.66 (m, 2H) 7.61 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.45 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.22 (d, 1 H, J = 8.4 Hz) 7.21 (s, 2H) 7.18 (d, 1 H, J = 7.6 Hz) 2.42 (s, 3H) MS (ESI, pos. Ion) m / z: 408.3 (M + 1).
Comp. Name and data 316 (E) -2-. { 2- [2- (3,4-dichloro-phenyl] -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide H-MN (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.84 (s, 1 H) 7.70-7.66 (m , 2H) 7.64 (d, 1 H) 7.60 (d, 2H, J = 7.6 Hz) 7.59 (s, 2H) 7.42 (dt, 2H, J = 1.6 and 9.2 Hz) 7.25 (d, 1 H, J = 16.4 Hz) 2.42 (s, 3H) MS (ESI, pos. Ion) m / z: 408.3 (M + 1). 317 (E) -2-. { 2- [2- (3-bromo-4-fluoro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.96 (dd, 1 H, J = 2 and 5 Hz) 7.69- 7.62 (m, 4H) 7.61-7.57 (m, 2H) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.39 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.29 (t, 1 H , J = 8.4 Hz) 7.18 (d, 1 H, J = 16.4 Hz) 2.40 (s, 3H) MS (ESI, pos. Ion) m / z: 486.2 (M). 318 (£) -2-. { 2- [2- (4-d.methylamino-phenyl) -v] n-1] -1 H-benzimidazol-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.96 (d, 1 H, J = 16.4 Hz) 7.73- 7.67 (m, 3H) 7.63 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.59 (d, 2H, J = 9.2 Hz) 7.52 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.44 (dd, 1 H, J = 1.6 and 7.6 Hz) 6.90 (d, 1 H, J = 16 Hz) 6.81 (d, 2H, J = 8.8 Hz) 3.06 (s, 6H) 2.45 (s, 3H) MS (ESI, ion pos .) m / z: 433.4 (M + 1). 319 (E) -2-. { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl] -vinyl] -1H-benzyldazole-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.6 and 6.4 Hz) 7.77 (q, 1 H, J = 5.3 Hz) 7.73- 7.63 (m, 5H) 7.60 (dt, 1 H, J = 1.6 and 8.4 Hz) 7.51 (dd, 1 H, J = 1.6 and 6.4 Hz) 7.43 (d, 2H, J = 8.4 Hz) 7.39 (d, 1 H, J = 16.8 Hz) 2.41 (s, 3H) MS (ESI, pos. Ion) m / z: 476.3 (M + 1). 320 (£) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 6.4 Hz) 8.01 (t, 1 H, J = 7.8 Hz) 7.90 (d, 1 H, J = 16.4 Hz) 7.70-7.65 (m, 3H) 7.61 -7.56 (m, 3H) 7.45 (d, 1 H, J = 16.8 Hz) 7.28 (dd, 1 H, J = 1.2 and 7.2 Hz 7.40 (d, 1 H, J = 1.2 and 7.2 Hz) 2.40 (s, 3H) MS (ESI, pos. Ion) m / z: 476.3 (M + 1). 321 (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.6 and 6.0 Hz) 7.86 (t, 1 H, J = 2.0 and 6.2 Hz) 7.73- 7.65 (m, 5H) 7.61 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.46 (dd, 1 H, J = 1.6 and 8.8 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.34 ( t, 1 H, J = 8.8 Hz) 7.22 (d, 1 H, J = 16.4 Hz) 2.42 (s, 3H) MS (ESI, pos. ion) m / z 442.3 (M + 1).
Comp. Name and data 322 (E) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.6 and 6.0 Hz) 7.86 (t, 1 H, J = 2.0 and 6.2 Hz) 7.73-7.65 (m, 5H) 7.61 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.46 (dd, 1 H, J = 1.6 and 8.8 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.34 (t, 1 H, J = 8.8 Hz) 7.22 (d, 1 H, J = 16.4 Hz) 2.42 (s, 3H) MS (ESI, pos. Ion) m / z: 442.3 (M + 1). 323 (E) -N-methyl-2-. { 2- [2- (2,3,4-trifluoro-phenyl] -vinyl] -1 H -benzimidazol-5-yl} 1 H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (d, 1 H, J = 7.6 Hz) 7.75 (d, 1 H, J = 16.8 Hz) 7.68-7.56 (m, 5H) 7.43 ( d, 1 H, J = 3.2 Hz) 7.34 (d, 1 H, J = 1.2 and 8.0 Hz) 7.33 (d, 1 H, J = 4.0 Hz) 7.22 (q, 1 H, J = 8.8 Hz) 2.38 ( s, 3H) MS (ESI, pos. ion) m / z: 444.4 (M + 1). 324 (E) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.87-7.82 (m, 2H) 7.72-7.58 (m, 5H) 7.46-7.42 ( m, 2H) 7.31 (d, 1 H, J = 16.4 Hz) 2.41 (s, 3H) MS (ESI, pos. ion) m / z: 444.4 (M + 1). 325 (E) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.95 (d, 1 H, J = 16.8 Hz) 7.74- 7.66 ( m, 3H) 7.63-7.59 (m, 2H) 7.47 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.44 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.39 (d, 1 H, J = 16.8 Hz) 7.34-7.70 (m, 2H) 2.42 (s, 3H) MS (ESI, pos. Ion) m / z: 426.4 (M + 1). 326 (E) -2-. { 2- [2- (2,5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.82 (d, 1 H, J = 16.4 Hz) 7.69- 7.64 ( m, 3H) 7.61-7.55 (m, 2H) 7.43 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.37 (dd, 1 H, J = 1.6 and 8.8 Hz) 7.33 (d, 1 H, J = 16.8 Hz) 7.26-7.15 (m, 2H) 2.39 (s, 3H) MS (ESI, pos. Ion) m / z: 426.4 (M + 1). 327 (E) -2-. { 2- [2- (2,6-difluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.90 (d, 1 H, J = 16.8 Hz) 7.71-7.58 ( m, 4H) 7.51 (d, 1 H, J = 16.8 Hz) 7.46-7.43 (m, 3H) 7.12 (t, 2H, J = 9.0 Hz) 2.41 (s, 3H) MS (ESI, pos. ion) m / z: 426.4 (M + 1).
Comp. Name and data 328 (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.68-7.56 (m, 5H) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.36 (dd, 1H, J = 1.6 and 8.8 Hz) 7.31-7.25 (m, 3H) 6.99-6.96 (m, 1 H) 2.39 (s, 3H) MS (ESI, pos. Ion) m / z: 426.3 (M + 1). 329 (E) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1H-benzamidazol-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.66-7.56 (m, 6H) 7.48-7.42 (m, 2H) 7.36-7.32 (m, 2H) 7.17 (d, 1H, J = 16.8 Hz) 2.38 (s, 3H) MS (ESI, pos. Ion) m / z: 426.4 (M + 1). 330 (E) -2-. { 2- [2- (4-Fluoro-2-tnfluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.25 (dd, 1H, J = 1.6 and 16.4 Hz) 8.16 (dd, 1 H, J = 1.2 and 9.2 Hz) 8.06 (dd) , 1 H, J = 1.2 and 7.6 Hz) 8.4 (d, 1 H, J = 1.2 Hz) 8.25 (dd, 1H, J = 0.8 and 8.0 Hz) 7.73-7.56 (m, 5H) 7.46 (dd, 1 H , J = 1.6 and 8.0 Hz) 7.65 (d, 1 H, J = 16.4 Hz) 2.46 (s, 3H) MS (ESI, pos. Ion) m / z: 476.4 (M + 1). 331 (E) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.02-7.98 (m, 2H) 7.18-7.56 (m, 4H) 7.45-7.40 (m, 2H) 7.38 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.26 (d, 1 H, J = 16.8 Hz) 2.39 (s, 3H) MS (ESI, pos. Ion) m / z: 476.4 (M + 1). 332 (E) -2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.10-8.05 (m, 2H) 7.84 (d, 1H, J = 16.8 Hz) 7.71-7.55 (m, 5H) 7.43 (dd) , 1 H, J = 1.6 and 7.2 Hz) 7.37 (d, 1 H, J = 16.8 Hz) 7.32 (dd, 1 H, J = 1.2 and 8.4 Hz) 2.37 (s, 3H) MS (ESI, pos. ) m / z: 476.5 (M + 1). 333 (E) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.24 (s, 2H) 7.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.94 (s, 1 H) 7.73- 7.55 (m, 5H) 7.45-7.40 (m, 2H ) 7.32 (dd, 1 H, J = 1.6 and 8.4 Hz) 2.38 (s, 3H) MS (ESI, pos. Ion) m / z: 526.4 (M + 1). 334 (£) -2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.27 (s, 1 H) 8.08-7.92 (m, 3H) 8.87 (d, 1 H, J = 8.4 Hz) 7.69-7.56 (m, 4H) 7.44 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.36-7.32 (m, 2H) 2.37 (s, 3H) MS (ESI, pos. ion) m / z: 526.4 (M + 1 ).
Comp. Name and data 335 (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1 H-benzimidazole-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (d, 1 H, J = 8.4 Hz) 7.93 (d, 1 H, J = 8.0 Hz) 7.81 ( d, 1 H, J = 16.4 Hz) 7.74-7.56 (m, 4H) 7.50-7.23 (m, 5H) 2.37 (s, 3H) MS (ESI, pos. ion) m / z: 442.4 (M + 1) . 336 (£) -2-. { 2- [2- (2-Chloro-6-fluoro-phenyl) -v] nyl] - H-benzimidazol-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.89 (d, 1 H, J = 16.8 Hz) 7.68- 7.55 (m, 4H) 7.45 (d, 1 H, J = 16.8 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.38-7.31 (m, 3H) 7.23-7.18 (m, 1 H ) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 442.4 (M + 1). 337 (£) -2-. { 2- [2- (2,4-dichloro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.51 (d, 1 H, J = 16.8 Hz) 7.88 ( d, 1 H, J = 8.0 Hz) 7.68-7.56 (m, 5H) 7.45-7.41 (m, 2H) 7.32 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.24 (d, 1 H, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z. 458.3 (M + 1). 338 (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.82 (t, 1 H, J = 1.8 Hz) 7.68- 7.49 (m, 7H) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.35 (d, 1 H, J = 7.6 Hz) 7.30 (dd, 1 H, J = 0.8 and 8.0 Hz) 7.21 (d, 1 H, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 468.3 (M + 1). 339 (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl] -vinyl) -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.40 (d, 1 H, J = 16.4 Hz) 8.08-8.06 (m, 2H) 8.01 (d, 1 H, J = 8.4 Hz) 7.89 (dd, 1 H, J = 2.4 and 8.4 Hz) 7.80-7.56 (m, 4H) 7.44 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.33 (dd, 1 H, J = 1.6 and 7.2 Hz) 7.26 (d, 1 H, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 442.3 (M + 1). 340 (É) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.76-7.72 (m, 2H) 7.66-7.54 (m, 4H) 7.42 (dd, 1 H, J = 0.8 and 7.2 Hz) 7.32-7.26 (m, 4H) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 502.3 (M + 1).
Comp. Name and data 341 (E) -N-methyl-2-. { 2- [2- (4-trifluoromethylthio-phenyl) -vinyl] -1 H-benzimidazol-5-yl} -1 H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (d, 2H, J = 8.8 Hz) 8.06 (dd, 1 H, J = 1.2 and 8.4 Hz) 8.06 (d, 2H, J = 8.8 Hz) 7.75-7.56 (m, 5H) 7.47 (d, 1 H, J = 16.4 Hz) 7.44 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.34 (dd, 1 H, J = 1.2 and 8.4 Hz) 2.38 (s, 3H) MS (ESI, pos. Ion) m / z: 522.3 (M + 1). (£) -N-methyl-2-. { 2- [2- (4-trifluoromethanesulfonyl-phenol) -vinyl] -1H-benzyldazole-5-yl} - Benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.75 (q, 4H, J = 10.6 Hz) 7.44- 7.55 (m, 5H) 7.43 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.33-7.28 ( m, 2H) 2.37 (s, 3H) MS (ESI, pos. ion) m / z: 490.3 (M + 1). 343 (E) -N-methyl-2-. { 2- [2- (2-t fluoromethy1-pheny1) vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.07 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.02 (dd, 1 H, J = 12.0 and 16.0 Hz) 7.98 (d, 1 H, J = 8.0 Hz) 7.77 (d, 1 H, J = 8.4 Hz) 7.72-7.62 (m, 4H) 7.57 (dt, 1 H, J = 1.6 and 8.4 Hz) 7.54 (t, 1 H, J = 7.6 Hz) 7.44 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.32 (dd, 1 H, J = 1.6 and 8. 4 Hz) 7.21 (d, 1 H, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z. 458.4 (M + 1). 344 (£) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} - 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.66-7.62 (m, 4H) 7.60-7.54 (m, 3H) 7.51 (d, 1 H, J = 8.0 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.31 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.28 (d, 1 H, J = 8.4 Hz) 7.25 ( d, 1 H, J = 16.8 Hz) 2.37 (s, 3H) MS (ESI, pos. ion) m / z: 474.4 (M + 1). 345 (£) -N-methyl-2-. { 2- [2- (4-Trifluoromethoxy-phenyl) -v] nyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.75 (d, 2H, J = 8.4 Hz) 7.69-7.64 (m, 3H ) 7.61 (d, 1 H, J = 8.0 Hz) 7.57 (dt, 1 H, J = 1.2 and 8.4 Hz) 7.42 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.33 (d, 3H, J = 10.0 Hz) 7.20 (d, 1 H, J = 16.4 Hz) 2.38 (s, 3H) MS (ESI, pos. Ion) m / z: 474.4 (M + 1). 346 (£) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1H-benzyldazole-5-yl} -N-methy1-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.03-8.05 (m, 2H) 7.87 (dd, 2H, J = 1.68 and 7.6 Hz) 7.66-7.55 (m , 4H) 7.45 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.43 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.38-7.30 (m, 3H) 7.22 (d, 1 H, J = 16.4 Hz ) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 425.3 (M + 1).
Comp. Name and data 347 (£) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.36-7.63 (m, 4H) 7.62-7.55 (m, 3H) 7.44 (d, 3H, J = 8.0 Hz) 7.31 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.19 (d, 1 H, J = 16.4 Hz) 2.36 (s, 3H) MS (ESI, pos. ) m / z: 425.3 (M + 1). 348 (E) -2-. { 2- [2- (2-bromo-pheny] -v-n-1] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.07 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.02 (d, 1 H, J = 16.4 Hz) 7.84 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.68-7.55 (m, 5H) 7.44-7.40 (m, 2H) 7.31 (dd, 1 H, J = 1.2 and 6.8 Hz) 7.02 (dt, 1 H, J = 1.6 and 8.4 Hz) 7.17 (d, 1 H, J = 16.4 Hz) 2.37 (s, 3H) MS (ESI, pos. ion) m / z: 469.5 (M + 1). 349 (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.06 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.80 (q, 1 H, J = 8.0 Hz) 7.74 ( d, 1 H, J = 16.8 Hz) 7.67-7.54 (m, 5H) 7.42 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.30 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.23 (d, 1 H, J = 16.8 Hz) 7.05 (t, 1 H, J = 8.8 Hz) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 426.4 (M + 1). 351 (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzyldazole-5-yl} -N-methy1-benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.07 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.01 (d, 2H, J = 8.4 Hz) 7.90 (d, 2H, J = 8.8 Hz) 7.72 (d, 1 H, J = 16.4 Hz) 7.67-7.56 (m, 4H) 7.44 (dd, 1 H, J = 1.6 and 7.2 Hz) 7.38 (d, 1 H , J = 16.4 Hz) 7.33 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.15 (s, 3H) 2.37 (s, 3H) MS (ESI, pos. Ion) m / z: 468.4 (M + 1) .
EXAMPLE 19 (E) -N- (2- 2-r 2 - (4-ethoxy-phenyl) -vinin-1 H-benzimidazol-5-yl) -phenyl) -methanesulfonamide (Compound 414) Step A tert-butyl ester of (3-tert-butoxycarbonylamino-2'-methanesulfonylamino-biphenyl-4-yl) -carbamic acid To a solution of Compound 16a (2.0 g, 5.1 mmol), 2-methylsulfonylphenyl boronic acid (1.1 g, 5.1 mmol), and K2CO3 (2.1g, 15.3 mmol) in 1.4-dioxane: water (4: 1, 120 mL), was added Pd (dppf) Cl2CH2Cl2 (0.42 g, 0.51 mmol) under an argon atmosphere. The mixture was heated at 95 ° C for 12 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc: hexanes, 3: 7) to give the title compound 19a as a yellow solid (1.7 g, 70% yield). 1 H NMR (400MHz, CDCl 3) d (ppm): 7.64 (d, J = 8.4 Hz, 1 H), 7.57 (d, J = 14.4 Hz, 1 H), 7.34 (t, J = 8.4 Hz, 1 H) , 7.26-7.15 (m, 3H), 7.07 (s, 1 H), 7.04 (d, J = 8 Hz, 1 H), 6.87 (s, 1 H), 6.63 (s, 1 H), 2.90 (s) , 3H), 1.51 (s, 9H), 1.49 (s, 9H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H31 N3O6S: 478.19 (M + H), Experimental 478.0.
Step B N- (3 ', 4'-diamino-biphenl-2-yl) -methanesulfonamide A solution of Compound 19a (1.0 g, 2.1 mmol) in a mixture of 4M HCl in 1,4-dioxane (10 mL) was heated to 70 ° C for 2 h. After concentration of the reaction, the residue was dissolved in dichloromethane (20 ml), and K2CO3 (0.5 g) was added to the solution and the mixture was stirred at room temperature for 20 min. After filtration and removal of solvents, the residue was dried to give the title compound 19b as a brown solid (0.58 g, quantitative yield). 1 H NMR (400MHz, CD 3 OD) d (ppm): 7.47 (d, J = 8.4 Hz, 1 H), 7.40-7.35 (m, 1 H), 7.32-7.29 (m, 2H), 7.16-7.09 (m, 3H), 2.80 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C13H15N302S: 278.09 (M + H), Experimental 278.1.
Step C (a-N- (2- {2-y2- (4-ethoxy-phenyl) -vinin-1 H-benzimidazol-5-yl) -fenin-methanesulfonamide A solution of Compound 19b (50 mg, 0.18 mmole) and acid 3- (4-ethoxy-phenyl) -acrylic commercially available (34.6 mg, 0.18 mmol) in POCI3 (1.5 mi) was heated at 100 ° C for 12 h. The reaction was cooled, the excess of POCI3 was removed under reduced pressure and the residue was purified by HPLC (Gilson, column C-18, CH3CN: H20 (gradient of CH3CN: 5% -80%)) to give the title compound 414 as a white solid (25 mg, 32% yield). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 7.62-7.59. (M, 4H), 7.54-7.52. (M, 1 H), 7.41-7.37 (m, 2H), 7.35-7.30 (m, 2H ), 7.03 (d, J = 16.8 Hz, 2H), 6.97 (d, J = 12 Hz, 2H), 4.09 (q, J = 7.2 Hz, 2H), 2.72 (s, 3H), 1.41 (t, J) = 7.2 Hz, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H23N303S: 434.1 (M + H), Experimental 434.1. By the procedures described in Example 19 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 77 (E) -N- (2- { 2- [2- (4-Chloro-phenyl) -v] nyl] -1 H -benzyldazole-5-yl.} - phenyl ) - 1H-NMR methanesulfonamide (400 Hz, CD3OD) d (ppm) 7.40-7.56 (m, 6H) 7.24-7.33 (m, 4H) 7.19-7.22 (m, 2H) 7.05 (d, J = 16.4Hz, 1 H) 2.61 (s, 3H). MS (ESI, pos. Ion) m / z: 424.1 (M + 1)., 83 (£) -N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H- benzimidazol-5-yl.} - phenyl) -methanesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 7.99-7.96 (m, 2H), 7.89-7.86 (m, 4H), 7.78 ( dd, J = 6.4, 15.8 Hz, 2H), 7.60 (dd, J = 1.2, 8.2 Hz, 1 H), 7.46- 7.39 (m, 2H), 7.33 (dt, J = 1.6, 8.2 Hz, 2H), 6.99 (dd, J = 6.4, 15.8 Hz, 2H), 3.10 (s, 10 3H), 3.09 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H2iN304S2: 468.1 (M + H), Experimental 468.0., 95 (£) -N- [2- (2- { 2- [4- (2.2 , 2-trifluoro-ethoxy) -phenyl] -vinyl] -H-benzimidazol-5-yl) -phenyl] -methanesulfonamide 1H NMR (400 MHz, CD3OD) d (ppm): 7.67 -7.62 (m, 5H), 7.54-15 7.52, (m, 1 H), 7.42-7.33 (m, 4H), 7.09 (d, J = 16.4 Hz, 2H), 7.08 (d, J = 12 Hz, 1 H), 4.60 (q, J = 8.4 Hz, 2H), 2.74 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C 24 H 20 F 3 N 3 O 3 S: 488.1 (M + H), Experimental 488.3, 101 (E) -N- [2- (2- { 2- [4- (2.2.3.3, 3-pentafluoro-propoxy) -phenyl] -vinyl.] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide H-NMR (400 MHz, 20 CD3OD) d (ppm): 7.65-7.60 (m, 5H), 7.54-7.52 (m, 1 H), 7.41-7.37 (m, 2H), 7.34-7.30 (m, 2H), 7.10-7.06 (m , 3H), 4.68 (t, J = 12.8 Hz, 2H), 2.74 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C25H20F5 3O3S: 538.1 (M + H), Experimental 538.2, Comp. Name and data 113 (E) -N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide 1 H-NMR (400 MHz, CD30D) d (ppm) 7.90-7.96 (m, 2H) 7.54-7.76 (m, 6H) 7.26-7.42 (m, 5H) 2.76 (s, 3H). MS (ESI, pos. Ion) m / z: 458.1 (M + 1)., 406 (E) -N- (2- { 2- [2- (4-bromo-phenyl) -vinyl] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 7.87-7.80 (m, 2H), 7.58-7.30 (m, 9H), 2.85 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H18BrN302S: 468.0 (M + H), Experimental 469.1, 407 (E) -N- (2- { 2- [2- (4- isopropyl-phenyl ) -vinyl] - H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide 1 H-NMR (400 MHz, CD3OD) d (ppm): 7.67-7.52) (m, 6H), 7.14 (d) , J = 16.4 Hz, 1 H), 3.13-3.12 (m, 1 H), 2.72 (s, 3H), 1.27 (d, J = 6.8 Hz, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C25H25N302S: 432.2 (M + H), Experimental 432.2, 408 (E) -N- (2- { 2- [2- (4- isopropyl-phenyl) - vinyl] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 7.82 (dd, J = 2.4, 7.2 Hz, 1 H) 7.66 -7.60 (m, 4H), 7.56-7.52 (m, 2H), 7.41-7.39 (m, 6H), 7.18 (d, J = 16.4 Hz, 1 H), 2.73 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H17CIFN302S: 442.1 (M + H), Experimental 442.3, Comp. Name and data 409 (£) -N- (2- { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1H-benzyldazole-5-yl. phenyl) -metanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 7.95 (dd, J-2.4, 6.8 Hz, 1 H), 7.69-7.68 (m, 1 H), 7.67-7.63 (m, 2H), 7.58 (d, J = 16.4 Hz, 1 H), 7.53-7.51 (m, 1 H), 7.40-7.26 (m, 5H), 7.18 (d, J = 16.4 Hz, 1 H), 2.72 ( s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H17BrF 302S: 486.0 (M + H), Experimental 486.3, 410 (E) -N- (2- { 2- [2- (4-difluoromethoxy-phenyl) -villin] -1 H- benzimidazol-5-yl.} - phenyl) - methanesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.73 (d, J = 12.8 Hz, 2H) , 10 7.54-7.52 (m, 1 H), 7.48-7.45 (m, 1 H), 7.41 -7.39 (m, 2H), 7.34-7.30 (m, 2H), 7.21 (d, J = 8.8 Hz, 2H) , 7.16 (d, J = 17.2 Hz, 1 H), 6.90 (s, 1 H), 2.73 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H19F2N303S: 456.1 (M + H), Experimental 456.1, 411 (E) -N- (2- { 2- [2- (3-fluoro-5- trifluoromethyl) -phenyl) -vinyl] -1H-benzimidazol-5-yl.}. -phenyl) -methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 7.77 (s, 1 H), 7.75 (d, J) = 12 Hz, 1 H), 7.68 (s, 1 H), 7.67-7.64 (m, 2 H), 7.52 (d, J = M Hz, 1 H), 7.46 (d, J = 12 Hz, 1 H) , 7.40-7.25 (m, 5H), 2.74 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H17F4N302S. 476.1 (M + H), Experimental 476.2, 412 (£) -N-. { 2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - 20 methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 7.65-7.60 (m, 3H), 7.41-7.36 (m, 3H), 7.41-7.36 (m, 2H), 7.33-7.30 (m, 2H), 7.26 (d, J = 10 Hz, 2H), 7.18 (d, J = 20 Hz, 1 H), 2.74 (s, 3H), 2.39 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H21N302S: 404.1 (M + H), Experimental 404.3, Comp. Name and data 413 (E) -N- (2- { 2- [2- (4-dimethylamino-phenyl) -v] nyl] -1H-benzimidazole-5-yl. 1) -methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 7.69-7.61 (m, 2H) 7.57-7.51 (m, 2H), 7.46-7.39 (m, 3H), 7.29 (d, J) = 16.2 Hz, 2H), 7.05 (d, J = 12 Hz, 1 H), 6.67 (d, J = 16.2 Hz, 2H), 6.33 (d, J = 12 Hz, 1 H), 3.01 (s, 3H) ), 2.97 (s, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H24N402S: 433.2 (M + H), Experimental 433.3, 415 (E) -N-. { 2- [2- (2-naphthalen-2-l-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.09 (s, 1 H), 7.96-7.88, 10 (m, 4H), 7.74-7.72 (m, 2H), 7.57-7.52 (m, 3H), 7.51-7.33 (m, 6H), 2.80 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C26H21N3O2S: 440.1 (M + H), Experimental 440.3, 416 (£) -N- (2- { 2- [2- (3,4-dichloro-phenyl ) -vinyl] -1 H-benzimidazol-5-yl.}. -phenyl) -methanesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.03-8.00 (m, 1 H), 7.93 (s, 1 H), 7.77 (s, 1 H), 7.74 (d, J = 1 1.2 Hz, 1 H), 7.69 (s, 1 H), 7.57-7.52 (m, 2H), 7.47 (d, J = 8 Hz , 1 H), 7.44 (d, J = 7.6 Hz, 2H), 7.40-7.36 (m, 1 H), 7.32 (d, J = 17.2 Hz, 1 H), 2.84 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C22Hl7CI2N302S: 458.0 (M + H), Experimental 458.2, Comp. Name and data 417 (E) -N- (2- { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl .}. -. phenyl) - methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.03-8.00 (m, 1 H), 7.76 (t, J = 8.0 Hz, 1 H), 7.71-7.67 (m , 3H), 7.63 (d, J = 8.4 Hz, 1 H), 7.54-7.52 (m, 1 H), 7.78-7.44 (m, 1 H), 7.43-7.38 (m, 3H), 7.38-7.32 ( m, 1 H), 2.77 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H17F4N302S: 476.1 (M + H), Experimental 476.2, 418 (E) -N- (2- { 2- [2- (2-fluoro-4-trifluoromethyl) -phenyl) -vinyl) -1 H- benzimidazol-5-yl} phenyl) -methanesulfonamide 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.00 (t, J = 8.4 Hz, 1 H), 7.84 (d, J = 17.2 Hz, 1 H), 7.62-7.58 (m , 2H), 7.55-7.52 (m, 2H), 7.46 (s, 1 H), 7.44- 7.38 (m, 3H), 7.38-7.32 (m, 2H), 2.74 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H17F4N302S: 476.1 (M + H), Experimental 476.2, 475 (£) -N-. { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide H-NMR (400 MHz, CDCl 3) d (ppm) 7.44-7.65 (m, 10H) 7.22-7.40 (m, 5H) 7.10-7.20 (m, 3H) 2.76 (s, 3H). MS (ESI, pos. Ion) m / z: 466.2 (M + 1)., PROPHETIC EXAMPLE 20 By the procedures described in Example 19, or by the procedures of Example 1 and the corresponding bromobenzimidazole and boronic acid or boronate ester and the reagents, starting materials and conditions known to those skilled in the art, they can prepare the following representative prophetic compounds of the present invention: Comp. Name and data 89 (£) -N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl.} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 107 (£) -N- (2- { 2- [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazole-5 -yl.}.-phenyl) -methanesulfonamide, 119 (E) -N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} .-phenyl) -metanesulfonamide, 125 (E) -C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1H-benzimidazol-2-yl] - vinyl.}. phenyl) -methanesulfonamide.
PROPHETIC EXAMPLE 21 By the procedures described in Example 1 or Example 19 and reagents, starting materials and conditions known to those skilled in the art, the following prophetic compounds can be prepared representative of the present invention: Comp. Name and data 72 (E) -C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -methanesulfonamide, 73 (E) -C, C, C-trifluoro-N- (2- {2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole- 5-yl.}.-Phenyl) -methanesulfonamide, 74 (£) -C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide. 75 (£) -1- (2- { 2- [2- (4-chloro-phenyl] -vinyl] -1 H -benzimidazol-5-yl}. Phenyl) -ethanone, 76 ( E) -1- (2- { 2- [2- (4-chloro-phenyl) -v-nyl) -1 H- benzimidazol-5-yl} phenyl) -ethanol, 80 (E) -N- (2- {2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) - C, C, C-trifluoromethanesulfonamide.
Comp. Name and data (£) -1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -vin] -1-H-benzimidazol-5-yl.} - phenyl) -ethanone, (E) -1- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H-benzimidazol-5-yl} -phenyl) -ethanol, (E) -1 - [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl] -1 H-benzimidazole- 5-yl) -phenyl] -ethanone, (£) -1 - [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, (E) -2- [2- (2- { 2- [4- (2,2,2-trifluoro-1- trifluoromethyl-ethoxy ) -phenyl] -vinyl.} -1 H -benzim'idazol-5-yl) -phenyl] -propan-2-ol, (£) -C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-1 -trifluoromethyl-ethoxy) - phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl. -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (E) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -pheny] - vinyl. -1 H-benzyldazole-5-yl) -pheny] -ethanol, (E) -2- [2- (2- { 2- [4- (2.2.2-trifluoro-ethoxy) -pheny] -vinyl.} -1H -benzimidazol-5-yl) -phenyl] -propan-2-ol, (E) -C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- ( 2,2,2-trifluoro-ethoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- [2- ( 2- {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (£) -1- [2- (2- { 2- [4- (2 >2,3,3,3-pentafluoro-propoxy!) - phenyl] -vill} -1H-benzimidazol-5-yl) -phenyl] -ethanol, (E) -2- [2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro- propoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol and (/) -CIC, C-trifluoro-N- [ 2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy!) -phenyl] -vinyl. -1 H-benzimidazole-5-yl) phenyl] -methanesulfonamide. (E) -1 - (2- { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzyldazole-5-yl.} -phenyl ) -etanone, (ZE) -1- (2- { 2- [2- (3-chloro-phenyl) -vinyl] -1 H- benzimidazol-5-yl.} - phenyl) - ethanol, (£) -2- (2- { 2- [2- (3-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2- ol, (E) -N- (2- { 2- [2- (3-chloro-phenyl) -v] n-1] -1H-benzimidazol-5-yl. L) -C, C, C-trifluoromethanesulfonamide, Comp. Name and data (E) -1- (2- { 2- [2- (3-trifluoromethy1-pheny1) -vin1] -1 H-benzimidazol-5-yl}. -phenyl] -ethanone, (E) -1- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl}. phenyl) -ethanol, (Z) -C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -vinyl] - H-benzyl) dazol-5-yl.}.-phenyl] -methanesulfonamide. (E) -N- (4- { 2- [5- (2-acetyl-pheny] -1 H- benzyldazol-2-yl) -vinyl} -pheny] -metanesulfonamide, (E) -N- [4- (2-. {5- [2- (1-Hydroxy-ethyl) -phenyl] -1H-benzamidazole -2-.l.] -vinyl) -phenyl] -methanesulfonamide, (E) -N- [4- (2-. {5- [2- (1-Hydroxy-1-methyl) -ethyl) -phenyl] -1H-benzimidazol-2-yl.] -vinyl) -phenyl] -methanesulfonamide (£) -C, C, C-trifluoro-N - (2- { 2- [2- (4-methanesulfonylamino-phenyl) -v-n-1] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) - N- (4-. {2- [5- (2-acetyl-phenyl) -1H-benzamidazole-2-yl] -vinyl] -phenyl] -C, C, C-tri fluoro-methanesulfonamide, (£) -ClC, C-trifluoro-N- [4- (2-. {5- [2- (1-Hydroxy-ethyl) -phenyl] -1H-benzimidazole-2 il.}. -vinyl) -phenyl] -methanesulfonamide, (£) -C, C, C-trifluoro-N- [4- (2- { 5- [2- (1-hydroxy-1-methyl- ethyl) -phenyl] -1H-benzimidazol-2-yl.] -vinyl) -phenyl] -methanesulfonamide and (£) -C, C, C-trifluoro-N- (4-. {2- [5- (2-trifluoromethanesulfoniamino-phenol) -1 H -benzimidazol-2-yl] -vinyl] -phenyl] -methanesulfonamide.
EXAMPLE 22 2-f2-r2- (2-trifluoromethyl-phenyl) -etin-1h-benzimida-2-yl-5-yl) -benzenesulfonamide (Compound 401) A mixture of Comp. 364 (E) -2-. { 2- [2- (2-Trifluoromethyl-phenyl] -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide (0.020 g, 0.045 mmol) and 10% palladium in carbon (0.005 g, 0.0045 mmol) in 2 ml of MeOH was hydrogenated under H2 gas [101.3 kPa (1 atm)] for 1 hour. The catalyst was removed by filtration, the filtrate was concentrated to dryness and the residue was purified by chromatography (silica gel, MeOH: CH2CI2 = 10: 1) to provide the title compound as a white solid.
H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6) Hz) 7.74-7.53 (m, 4H) 7.60-7.56 (m, 2H) 7.51-7.40 (m, 4H) 3.41 (m, 4H) MS (ESI, pos. Ion) m / z: 446.5 (M + 1).
Through the procedures described in Example 22 and reagents, starting materials and conditions known to the experts in the art, the following representative compounds of the present invention were prepared invention from the corresponding vinyl derivatives: Comp. Name and data 129 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, 1.2 and 8.0 Hz) 7.65-7.54 (m, 4H) 7.44-7.31 (m, 4H) 7.20 (d, 2H, J = 8.8 Hz) 3.26-3.23 (m, 4H) MS (ESI, pos. Ion) m / z: 462.4 (M + 1). 130 2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.64-7.51 (m, 6H) 7.42 (d, 2H, J = 8.0 Hz) 7.39 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.27 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.24 (m, 4H) MS (ESI, pos. ion) m / z: 446.4 (M + 1 ). 131 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, J = 1.2 and 8.0 Hz) 8.02 (d, 2H, J = 8.8 Hz) 7.70- 7.55 (m, 7H) 7.42 (dd, 1 H, J = 1.6 and 7.2 Hz) 7.36 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.41-3.48 (m, 4H) MS (ESI, pos. ion) m / z: 510.2 (M +1) 139 2-. { 2- [2- (4-chloro-phenyl) -ethyl] -1 H- benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (dd, 1 H, 1.6 and 8.0 Hz) 7.64-7.59 (m, 2H) 7.55-7.51 (m, 2H) 7.39 (dd, 1 H, J = 0.8 and 7.6 Hz) 7.32-7.14 (m, 5H) 3.20-3.13 (m, 4H) MS (ESI, pos. Ion) m / z: 412.3 (M + 1).
Comp. Name and data 145 2-. { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, 1.2 and 7.6 Hz) 7.87 (d, 2H, J = 8.4 Hz) 7.66-7.50 (m, 6H) 7.41 (dd) , 1 H, J = 1.2 and 8.0 Hz) 7.30 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.10 (m, 4H) MS (ESI, pos. Ion) m / z: 456.3 (M + 1). 175 2-. { 2- [2- (3-trifluoromethyl-phenyl] -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide? -RMN (400 MHz, CD3OD) d (ppm): 8.13 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.70-7.48 (m, 8H) 7.44 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.39 (dd, 1 H, J = 1.2 and 7.2 Hz) 3.40-3.30 (m, 4H) MS (ESI, pos. Ion) m / z: 446.4 (M + 1). 383 2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl} 1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.02 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.52-7.49 (m, 2H) 7.45-7.41 (m, 4H) 7.31-7.26 ( m, 1 H) 7.18 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.13 (t, 1 H, J = 7.2 Hz) 3.20-3.15 (m, 4H) MS (ESI, pos. ion) m / z : 446.4 (M + 1). 384 2-. { 2- [2- (2,3,4-trifluoro-phenyl) -ethyl] -1H-benzamdazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.66-7.53 (m, 4H) 7.42 (dd, 1 H, J = 1.6 and 7.6 Hz) 7.29 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.04-6.99 (m, 2H) 3.24 (m, 4H) MS (ESI, pos. Ion) m / z: 432.5 (M + 1). 385 2-. { 2- [2- (2,4,5-trifluoro-phenyl) -ethyl] -1H-benzimidazol-5-yl} - 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.4 Hz) 7.67-7.53 (m, 4H) 7.42 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.30 (dd, 1 H, J = 1.6 and 8.4 Hz) 7.26-7.10 (m, 2H) 3.23-3.20 (m, 4H) MS (ESI, pos. Ion) m / z: 432.3 (M + 1) . 386 2-. { 2- [2- (2,6-d.fluoro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.67-7.53 (m, 4H) 7.42 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.31-7.25 (m, 2H) 6.97-6.93 (m, 2H) 3.26-3.19 (m, 4H) MS (ESI, pos. Ion) m / z: 414.3 (M + 1). 387 2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (dd, 1 H, 1.6 and 8.0 Hz) 7.92 (dd, 1 H, 1.2 and 8.4 Hz) 7.80 (s, 1 H) 7.64-7.51 (m, 4H) 7.40-7.33 (m, 2H) 7.28 (dd, 1 H, J = 1.6 and 8.0 Hz) 3.38-3.25 (m, 4H) MS (ESI, pos. ion) m / z: 514.4 (M +1) Comp. Name and data 388 2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl] -etl] -1 H-benzimidazol-5-yl} -benzenesulfonamide 1H-MN (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.94 (d, 1 H, J = 8.0 Hz) 7.76- 7.72 (m, 2H) 7.67-7.54 (m, 4H) 7.42 (dd, H, J = 1.2 and 7.6 Hz) 7.33 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.50-3.45 (m, 2H) 3.31 - 3.26 (m , 2H) MS (ESI, pos. Ion) m / z: 514.5 (M + 1). 390 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (dd, 1 H, 1.6 and 8.0 Hz) 7.54-7.60 (m, 3H) 7.54 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.52-7.48 (m, 2H) 7.43 (dd, 1 H, J = 2.0 and 8.4 Hz) 7.39 (dd, 1 H, J = 1.6 and 7.2 Hz) 7.27 (d, 1 H, J = 8.0 Hz) 3.23 (m, 4H) MS (ESI, pos. Ion) m / z: 480.4 (M + 1). 391 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, 1.2 and 8.0 Hz) 7.65-7.54 (m, 4H) 7.43-7.37 (m, 2H) 7.33 (dd, 1 H , J = 2.0 and 8.0 Hz) 7.26 (d, 1 H, J = 8.8 Hz) 7.17 (s, 1 H) 7.13 (d, 1 H, J = 9.6 Hz) 3.26 (m, 4H) MS (ESI, ion pos.) m / z: 462.4 (M + 1). 392 2-. { 2- [2- (2,4-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, 1.6 and 6.4 Hz) 7.67-7.53 (m, 4H) 7.42 (dd, 1 H, 1.6 and 8.0 Hz) 7.30 ( dd, 1 H, J = 1.2 and 6.8 Hz) 7.28-7.23 (m, 1 H) 6.96-6.85 (m, 2H) 3.22 (m, 4H) MS (ESI, pos. ion) m / z: 414.2 (M +1) 393 2-. { 2- [2- (3,4-difluoro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1H, 1.2 and 7.6 Hz) 7.65-7.53 (m, 4H) 7.42 (dd, 1 H, 1.2 and 7.2 Hz) 7.32 (dd) , 1 H, J = 1.2 and 8.4 Hz) 7.22-7.13 (m, 2H) 7.04-7.01 (m, 1 H) 3.22 (m, 4H) MS (ESI, pos. Ion) m / z: 414.4 (M + 1 ). 394 2-. { 2- [2- (2,3-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1 H, 1.6 and 8.0 Hz) 7.68-7.53 (m, 4H) 7.42 (dd, 1 H, 1.6 and 7.6 Hz) 7.32 ( dd, 1 H, J = 1.6 and 8.0 Hz) 7.15-7.01 (m, 3H) 3.28 (m, 4H) MS (ESI, pos. ion) m / z: 414.3 (M + 1). 395 2-. { 2- [2- (2,5-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide H-NMR (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, 2.4 and 7.6 Hz) 7.67-7.53 (m, 4H) 7.43-7.39 (m, 1 H) 7.33-7.29 (m , 1 H) 7.12-6.94 (m, 3H) 3.26 (m, 4H) MS (ESI, pos. Ion) m / z: 414.4 (M + 1).
Comp. Name and data 396 2-. { 2- [2- (3,5-difluoro-phenyl) -ethyl) -1 H- benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, 2.0 and 8.0 Hz) 7.67-7.54 (m, 4H) 7.42 (dd, 1 H, 1.6 and 7.6 Hz) 7.36 ( dd, 1 H, 1.6 and 8.4 Hz) 6.91-6.77 (m, 3H) 3.26-3.20 (m, 4H) MS (ESI, pos. ion) m / z: 414.6 (M + 1). 397 2- (2-phenethyl-1H-benzamdazol-5-yl) -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (dd, 1H, 1.6 and 7.6 Hz) 7.67 -7.54 (m, 4H) 7.42 (dd, 1H, 1.6 and 7.6 Hz) 7.30-7.17 (m, 7H) 3.25-3.06 (m, 4H) MS (ESI, pos. Ion) m / z: 378.3 (M + 1 ). 399 N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide The title compound was prepared by hydrogenation using Compound 398. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.07 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.65 (dt, 1 H , J = 1.6 and 8.2 Hz) 7.58-7.53 (m, 5H) 7.41-7.38 (m, 3H) 7.20 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.25 (m, 4H) 2.27 (s, 6H) MS (ESI, pos. Ion) m / z: 474.4 (M + 1). 402 2-. { 2- [2- (2-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -1-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.12 (d, 1 H) 7.64-7.52 (m, 4H) 7.41-7.38 (m, 2H) 7.26-7.19 (m, 4H) 3.22-3.18 (m, 4H) MS (ESI, pos. ion) m / z: 412.3 (M + 1). 404 2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.12 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.64-7.60 (m, 2H) 7.56-7.51 (m, 2H) 7.46-7.38 ( m, 3H) 7.30-7.27 (m, 2H) 3.33-3.30 (m, 2H) 3.35-3.32 (m, 2H) MS (ESI, pos. ion) m / z: 464.4 (M + 1). 405 2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazole-5-yl} -1 H-NMR (400 MHz, CD3OD) d (ppm): 8.15 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.66-7.62 (m, 2H) 7.59-7.50 (m, 4H) 7.41 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.31 (dd, 1 H, J = 1.6 and 8.0 Hz) 7.26-7.21 (m, 1 H) 3.26 (m, 4H) MS (ESI, pos. Ion) m / z : 464.3 (M + 1).
Comp. Name and data 2-. { 2- [2- (2-Fluoro-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.14 (d, J = 8.0 Hz, 1 H), 7.71 (s, 1 H), 7.68-7.64 (m, 2H), 7.60- 7.57 (m, 1 H), 7.40 (d, J = 8.0 Hz, 1 H), 7.48 (d, J = 8.0 Hz, 1 H), 7.29-7.24 (m, 2H), 7.12-7.06 (m, 2H) ), 3.41 (t, J = 8.0 Hz, 2H), 3.28 (t, J = 8.0 Hz, 2H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH18FN302S: 396.1 (M + H), Experimental 396.3. 2-. { 2- [2- (4-fluoro-phenyl) -etl] -1 H-benzimidazole-5-yl} 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.14 (dd, J = 1.6, 8.0 Hz, 1 H), 7.73 (s, 1 H), 7.69 (d, J = 8.0 Hz, 1 H ), 7.65 (dd, J = 1.6, 8.0 Hz, 1 H), 7.58 (dt, J = 1.6, 8.0 Hz, 1 H), 7.51 (d, J = 1.6, 8.0 Hz, 1 H), 7.40 (dd) , J = 1.2, 7.2 Hz, 1 H), 7.27-7.24 (m, 2H), 7.04-7.00 (m, 2H), 3.42 (t, J = 8.0 Hz, 2H), 3.23 (t, J = 8.0 Hz , 2H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH18FN302S: 396.1 (M + H), Experimental 396.3. 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm): 8.12 (d, J = 8.0 Hz, 1 H), 7.64-7.60 (m, 2H), 7.56-7.51 (m, 2H), 7.40-7.36 (m, 2H), 7.32-7.29 (m, 3H), 3.27-3.25 (m, 4H). Mass spectrum (LCMS, ESI pos.) Calculated for C22H17F4N3C > 2S: 464.1 (M + H), Experimental 464.3. 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} 1 H-NMR-benzenesulfonamide (400 MHz, CD3OD) d (ppm): 8.12 (dd, J = 1.6, 8 Hz, 1 H), 8.01 (d, J = 1.6, 8 Hz, 1 H), 7.65-7.60 ( m, 3H), 7.58-7.53 (m, 3H), 7.48-7.44 (m, 1 H), 7.40 (dd, J = 1.6, 8 Hz, 1 H), 7.33 (dd, J = 1.6, 8 Hz, 1 H), 3.13 (m, 1 H), 2.86 (t, J = 7.6 Hz, 2H), 2.83 (t, J = 7.6 Hz, 2H), 1.21 (d, J = 7.6 Hz, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H25N302S: 420.5 (M + H), Experimental 420.4. 4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide The title compound was prepared by hydrogenation using Compound 444. H-NMR (400 MHz, CD3OD) d (ppm): 8.33 (d, J = 8 Hz, 1 H), 7.83 (dd, J = 2 , 8 Hz, 1 H), 7.63 (d, J = 8 Hz, 2H), 7.58-7.54 (m, 3H), 7.42 (d, J = 8 Hz, 2H), 7.29 (dd, J = 2, 8 Hz, 1 H), 3.28-3.24 (m, 4H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H17F6N302S: 514.5 (M + H), Experimental 514.3.
Comp. Name and data 447 4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide The title compound was prepared by hydrogenation using Compound 446. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.42 (s, 1 H), 7.94 (d, J = 8 Hz, 1 H) , 7.63-7.56 (m, 5H), 7.42 (d, J = 8 Hz, 2H), 7.29 (d, J = 1.6, 8 Hz, 1 H), 3.27-3.25 (m, 4H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H17F6N302S: 514.1 (M + H), Experimental 514.2.
EXAMPLE 23 N-methyl-2 ^ 2-r2- (4-trifluoromethyl-phenyl) ^ tin-1 H-benzimidazol-5-yl > - benzenesulfonamide (Compound 400) By the procedure of Example 18, the compound of title was prepared from Compound 18c and 4-trifluoromethylphenyl acid propionic 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.04 (dd, 1 H, J = 1.2 and 8.0 Hz) 7.66-7.53 (m, 6H) 7.42-7.38 (m, 3H) 7.29 (dd, 1 H, J = 1.6 and 8.4 Hz) 3.27 (m, 4H) MS (ESI, pos. Ion) m / z: 460.4 (M + 1).
EXAMPLE 24 N-methyl-2-f2-r2- (3-trifluoromethyl-phenyl) -etill-1 H-benzimidazol-5-yl > - benzenesulfonamide (Compound 350) By the procedure of Example 18, the title compound was prepared from Compound 18c and 3-trifluoromethylphenyl propionic acid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.05 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.64 (td, 1 H, 1.2 and 8.2 Hz) 7.58-7.53 (m, 4H) 7.50- 7.44 (m, 3H) 7.40 (dd, 1 H, J = 1.2 and 7.2 Hz) 7.25 (dd, 1 H, J = 1.6 and 8.0 Hz) 3.26-3.22 (m, 4H) MS (ESI, pos. Ion) m / z: 460.4 (M + 1).
EXAMPLE 25 2- (2 2-r 2 - (4-trifluoromethyl-phenyl) -ethyl-1 H-benzimidazol-5-yl-phenyl) -propan-2-ol (Compound 464) By the procedure of Example 10, the title compound 464 (0.013 g) was prepared from Compound 25a 5-bromo-2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazole (0.048 g , 0.13 mmole) and Compound 10e (0.032 g, 0.20 mmole). 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 7.71 (dd, J = 1.26.8.08 Hz, 1 H) 7.45 (d, J = 7.8 Hz, 2 H) 7.37 (d, J = 8.34 Hz, 1 H ) 7.31 (d, J = 8.08Hz, 2H) 7.20-7.26 (m, 2H) 7.10 (ddd, J = 1.51, 7.33, 7.58Hz, 1 H) 6.93-7.20 (m, 2H) 3.14 (m, 4H) 1.21 (s, 6H). MS (ESI, pos. Ion) m / z: 425.1 (M + 1). Using the procedures described in Example 25 and Compound 25a, and reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared from the corresponding vinyl derivatives: Comp. Name and data 457 N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.}. -phenyl) -acetamide 1 H-NMR (400 MHz , CD3OD)? (ppm): 7.50- 7.60 (m, 5H) 7.32-7.44 (m, 5H) 7.22-7.26 (d, J = 8.6Hz, 1 H) 3.24-3.30 (s, 4H) 1.96 (s, 3H). MS (ESI, pos. Ion) m / z: 424.2 (M + 1).
PROPHETIC EXAMPLE 26 By the procedures of Examples 22, 23, 24 or 25, and reagents, starting materials and conditions known to those skilled in the art, the following representative prophetic compounds of the present invention can be prepared: Comp. Name and data 133 C, C, C-trifluoro-N- (2- {2- [2- (4- trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - phenyl) -metanesulfonamide, 134 C, C, C-trifluoro-N- (2 { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -H-benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 135 1 - (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 1- (2- (2- {.2- [2- (4-Chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -ethanol, 137 N- (2-. {2- 2- [2- (4-Chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 138 2- (2- { 2- [2- (4-chloro-phenyl) - ethyl] -1H-benzimidazol-5-yl.}. -phenyl) -propan-2-ol, Comp. Name and data 140 N- (2- { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl] -C, C, C -trifluoro-methanesulfonamide, 141 1- (2- {2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanone, 142 1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 143 N- (2-. { 2- [2- (4-methanesulfonyl-phenyl] -ethyl] -1H-benzimidazol-5-yl] -phenyl) -methanesulfonamide, 2- (2-. {2- 2- [2 - (4-methanesulfonyl-phenyl] -etl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 146 C, C, C-trifluoro-N- (2. {2- [2- (4-methanesulfonyl-phenyl) -etl] -1 H -benzimidazol-5-yl. phenyl) -methanesulfonamide, 147 1 - [2- (2- { 2- [4- (2, 2, 2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl .} -1 H-benzyldazole-5-yl) -phenyl] -ethanone, 148 1 - [2- (2- { 2- [4- (2,2,2- trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 149 N- [2- (2-. {2 - [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzyldazole-5-yl) -phenyl ] -methansulfonamide, 150 2- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl. -1H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 151 2- (2-. {2- 2- [4- (2,2,2-trifluoro-1 - trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzyldazol-5-yl) -benzenesulfonamide, 152 C, C, C-trifluoro-N- [2- (2 - { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl} -1-H-benzimidazol-5-yl) -phenyl] - methanesulfonamide, 153 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazole-5-yl) -phen L] -etanone, 154 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -pheny] -ethyl.} -1 H-benzimidazol-5-yl ) -phenyl] -ethanol, 155 N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazole-5-yl) -phenyl] -methanesulfonamide, 156 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, Comp. Name and data 157 2- (2- { 2- [4- (2, 2, 2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide , 158 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 159 1- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-5-propoxy) -phenyl] -ethyl.} -1 H-benzimidazole-5- il) -phenyl] -ethanone, 160 1- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.}. -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 161 N- [2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propox !) -phenyl] -etyl! -1-H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 162 2- [2- (2- { 2- [4- (2, 2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} - 1 H -benzimidazol-5-yl) -phenyl] -10 propan-2-ol, 163 2- (2-. {2 - [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 164 C, C, C -trifluoro-N- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl) -etl} -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 165 1- (2-. {2- 2- [3 (3-chloro-phenyl) -etl] -1 H - benzimidazol-5-yl.} - phenyl] -ethanone, 166 1- (2- { 2- [2- (3-chloro-phenyl) -etl] -1 H-1 benzyl Midazol-5-yl.} - phenyl] -ethanol, 167 N- (2-. {2- 2- [2- (3-chloro-pheny] -ethyl] -1 H-benzimidazole-5 -yl.}.-phenyl) -methanesulfonamide, 168 2- (2- { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzyldazole-5-yl} -phenyl) -propan-2-ol, 169 2-. { 2- [2- (3-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 170 N- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl] -C, C, C-Trifluoromethanesulfonamide, 20 171 1- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H-benzyl-2-azole-5-yl! 1.}.-phenyl) -ethanone, 172 1- (2-. {2- [2- (3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl. .phenyl) -ethanol, 173 N- (2. {2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl}. phenyl) -methanesulfonamide, Comp. Name and data 174 2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol , 176 C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl} -1 H -benzimidazol-5-yl} - phenyl) - methanesulfonamide, 177 N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -ethyl] -phenyl) -methanesulfonamide, 178 N- [4- (2- { 5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazol-2-yl}. -ethyl) -phenyl] -methanesulfonamide, 179 N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl] -methanesulfonamide, 180 N- [4- (2- {5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -ethyl) -phenyl] -methanesulfonamide, 181 2-. { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 182 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -metanesulfonamide, 183 N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -ethyl} -phenyl) -C, C, C-trifluoro methanesulfonamide, 184 C, C, C-trifluoro-N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazol-2-yl}. ethyl) -phenyl] -methanesulfonamide, 185 C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl) -ethyl} phenyl) -methanesulfonamide, 186 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazole -2-yl.} - ethyl) -phenyl] -methanesulfonamide, 187 2-. { 2- [2- (4- Trifluoromethanesulfonylamino-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, and 188 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethanesulfonylamino-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -metansulfonamide.
EXAMPLE 27 2-. { 2-f2- (4-trifluoromethyl-phenyl) -cyclopropin-1H-benzimidazol-5-yl-benzenesulfonamide (Compound 190) Step A 2- (4-trifluoromethyl-phenyl) -cyclopropane-carboxylic acid methyl ester To a solution of trimethylsulfonium iodide (0.53 g, 2.39 mmol) in 8 mL of DMSO was added sodium hydride (0.06 g, 2.39 mmol) at 25 ° C. ° C. After stirring for one hour, a solution of methyl 4-trifluoromethylcinnamate (0.50 g, 2.17 mmol) in 4 ml of DMSO was added. The reaction mixture was stirred for six hours, then quenched by a saturated solution of NH 4 Cl. The resulting mixture was extracted with CH2Cl2, the organic phase was dried with Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica gel, hexanes: EtOAc, 2: 1) to give the title compound 27a as a solid.
Step B 2- (4-Trifluoromethyl-phenyl) -cyclopropanecarboxylic acid A solution of Compound 27a in 10 mL of MeOH and 4 mL of 1 N LiOH (ac) was heated at 70 ° C for 4 h. The mixture was then acidified by 4N HCl (aq) and extracted with EtOAc. The organic phase was washed with brine, dried with Na 2 SO 4 filtered and the filtrate was concentrated to give the title compound 27b. H-NMR (400 MHz, CD3OD) d (ppm): 7.56 (d, 2H) 7.25 (d, 2H) 2.39 (m, 1 H) 1.80 (m, 1 H) 1.47 (m, 1 H) 1.18 (m , 1 HOUR).
Step C 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl-1 H-benzimidazol-5-yl) -benzenesulfonamide To a solution of Compound 16c (0.140 g, 0.438 mmol) and Compound 27c N- (3- hydrochloride) dimethylammonopropyl) -N'-ethylcarbodiimide (0.060 g, 0.313 mmol) in 4 ml of acetonitrile was slowly added a solution of Compound 27b (0.072 g, 0.313 mmol) in 2 ml of acetonitrile. After stirring for 2 hours, the mixture was passed through a short column (silica gel, hexanes: EtOAc, 2: 1). The collected eluent was concentrated and the residue was dissolved in AcOH. The reaction was heated at 80 ° C for 3 h. The reaction was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 2: 1). This material was dissolved in TFA, and the mixture was heated at 60 ° C for 2 h. The reaction was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 1: 1) to give the title compound 190 as a solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 8.14 (dd, 1 H, J = 1.2 and 7.6 Hz) 7.74-7.63 (m, 6H) 7.60-7.47 (m, 5H) 7.40 (dd, 1 H , J = 1.6 and 7.2 Hz) 2.97-2.92 (m, 1 H) 2.76-2.71 (m, 1 H) 2.12-2.00 (m, 2H) MS (ESI, pos. Ion) m / z: 458.3 (M + 1).
EXAMPLE 28 2- (2- 2 -R2- (4-trifluoromethyl-phenyl) -cyclopropin-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol (Compound 471) Step A N-methoxy-N-methyl-3- (4-trifluoromethyl-phenyl) -acrylamide To a solution of 4-trifluoromethyl cinnamic acid (3.6 g, 16.7 mmol) in anhydrous methylene chloride (40 ml) oxalyl chloride was added slowly (1.7 ml, 19.5 mmol). To the solution anhydrous dimethylformamide (10 plitros) was added and the reaction was stirred at room temperature under argon atmosphere. After 18 h, the reaction was concentrated. A solution of the residue Compound 10b (16.7 mmol) in methylene chloride (40 ml) was added dropwise to a solution of β, β-dimethylhydroxylamine hydrochloride (1.6 g, 16.7 mmol) and triethylamine (5.8 ml, 41.7 mmol) in methylene chloride (40 ml) at 0 ° C. The reaction mixture was stirred at 0 ° C for 30 min, then warmed to room temperature. After 6 h, the reaction was washed successively with sodium carbonate (10% in water), water and brine. The organic fraction was dried with magnesium sulfate, filtered and the filtrate was concentrated. The Compound was purified by chromatography (silica, EtOAc: hexanes, 1: 1) to provide the title compound 28a (2.2 g, 50% over two steps) 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 7.96 ( d, J = 8.3Hz, 2H) 7.78 (d, J = 8.08Hz, 2H) 7.64 (d, J = 15.9Hz, 1H) 7.24 (d, J = 15.9Hz, 1H) 3.77 (s, 3H) 3.23 (s, 3H).
Step B 2- (4-Trifluoromethyl-phenyl) -cyclopropanecarboxylic acid methoxy-methyl acid. Anhydrous dimethyl sulfoxide (8 ml) was added dropwise under an argon atmosphere to a mixture of sodium hydride (suspension 60% in oil, 0.369 g. , 9.2 mmol) and trimethylsulfoxonium iodide (2 g, 9.1 mmol). Compound 28a (1.2g, 4.6 mmol) in DMSO (8 ml) was added dropwise to the solution. The reaction mixture was stirred at room temperature for 18 h. The reaction was poured into ethyl ether: water (1: 1, 50 ml). The organic phase was separated and washed successively with water and brine. The organic fraction was dried with magnesium sulfate, filtered and the filtrate was concentrated to give the title compound 28b (1.9 g, 90%). 1 H-NMR (400 MHz, CDCl 3) d (ppm) 7.55 (d, J = 8.08 Hz, 2 H) 7.25 (d, J = 8.3 Hz, 2 H) 3.72 (s, 3 H) 3.26 (s, 3 H) 2.54-2.59 (m, 1 H) 2.43-2.52 (m, 1 H) 1.68-1.74 (m, 1 H) 1.33-1.38 (m, 1 H).
Step C. 2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid To a solution of Compound 28b (3.6g, 13.2 mmol) in tetrahydrofuran (45 ml) was added a solution of potassium t-butoxide (M in tetrahydrofuran, 50 ml, 50 ml). mmoles). Water (1.5 ml, 83.3 mmol) was added to the reaction, and the reaction was stirred at room temperature under an argon atmosphere. After 18 h, ice was added to the reaction until it became homogeneous. Ethyl ether was added to the solution and the phases were separated. The aqueous phase was cooled and acidified with 1 M HCl until the pH was 4. The aqueous phase was extracted with ethyl acetate. The ethyl acetate phase was washed successively with water and brine. The organic phase was dried with magnesium sulfate, filtered and the filtrate was concentrated to give the title compound 28c (2.2 g, 73%). 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 12.4 (s, 1 H) 7.62 (d, J = 8.08 Hz, 2 H) 7.40 (d, J = 8.08 Hz, 2 H) 2.46-2.54 (m, 1 H) 1.88-1.96 (m, 1 H) 1 .46-1.52 (m, 1 H) 1.38-1.44 (m, 1 H).
Step D 5-Bromo-2- [2- (4-trifluoromethyl-phenyl) -cyclopropin-1 H-benzimidazole. By the procedure of Example 1, the title compound 28d was prepared from Compound 28c and 4-bromobenzene-1.2. -diamina. 1 H NMR (400 MHz, DMSO d 6) d (ppm) 7.96 (s, 1 H) 7.68-7.75 (m, 3H) 7.60-7.64 (dd, J = 1.5, 8.6Hz, 1 H) 7.46-7.56 (m , 4H) 7.10-7.14 (d, J = 8.4Hz, 2H) 2.96-3.02 (m, 1 H) 2.70-2.78 (m, 1 H) 2.10-2.16 (m, 1 H) 2.00-2.08 (m, 1 H).
Step E 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl-1 H-benzimidazol-5-yl) -phenyl) -propan-2-ol By the procedure of Example 10 , the title compound 471 was prepared from Compound 28d and Compound 10e. 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 12.4 (s, 0.5H) 12.32 (s, 0.5H) 7.88 (m, 1 H) 7.65 (d, 2H, J = 8.084 Hz) 7.46 (m, 2H ) 7.35 (m, 2H) 7.20 (m, 1 H) 6.95 (m, 2H) 4.85 (s, 1 H) 2.70 (m, 1 H) 2.46 (m, 1 H) 1.90 (m, 1 H) 1.70 (m, 1 H) 1 .20 (d, 6H). MS (ESI, pos. Ion) m / z: 437.2 (M + 1). Using the procedures described in Example 28 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared invention from the corresponding vinyl derivatives: Comp. Name and data 198 2- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.}. -phenyl) -propan-2-ol, H- MN (400 MHz, CD3OD) d (ppm) 7.83-7.86 (m, 1H) 7.44-7.49 (bs, 1H) 7.31-7.36 (m, 4H) 7.21-7.26 (m, 3H) 7.055-7.13 (m, 2H ) 2.60-2.65 (m, 1H) 2.40-2.44 (m, 1H) 1.84-1.90 (m, 1H) 1.62-1.70 (m, 1H) 1.32 (s, 6H). MS (ESI, pos. Ion) m / z: 403.2 (M + 1). 234 2- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol H-NMR (400 MHz , CD30D) d (ppm) 7.71-7.74 (dd, J = 1.01, 8.08Hz, 1H) 7.40-7.45 (m, 4H) 7.33-7.38 (d, J = 8.34Hz) 7.21-7.26 (m, 2H) 7.08 - 7.13 (ddd, J = 1.52, 7.58Hz, 1H) 6.99-7.02 (dd, J = 1.52, 8.34Hz) 6.93-6.97 (dd, J = 1.52, 7.58Hz, 1H) 2.60-2.66 (m, 1H) 2.37-2.42 (m, 1H) 1.78-1.84 (m, 1H) 1.59-1.65 (m, 1H) 1.22 (s, 6H). MS (ESI, pos. Ion) m / z: 437.3 (M + 1). 467 N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide 1H-NMR (400 MHz, CD3OD) d (ppm) 7.52-7.62 (m, 5H) 7.33-7.41 (m, 4H) 7.24-7.32 (m, 2H) 2.70 (m, 4H) 2.48-2.53 (m, 1H) 1.90-1.96 (m, 1H) 1.69 -1.75 (m, 1H). MS (ESI, pos. Ion) m / z: 472.2 (M + 1), 472 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - phenol 1 H-NMR (400 MHz, CD 3 OD) d (ppm) 7.70 (bs, 1 H) 7.61 (d, 2 H, J = 8.34 Hz) 7.51 (m, 3 H) 7.42 (m, 3 H) 7.30 (m, 1 H) 7.15 (m, 1H) 6.93 (m, 2H) 2.72 (m, 1H) 2.50 (m, 1H) 1.93 (m, 1H) 1.74 (m, 1H). MS (ESI, pos. Ion) m / z.395.2 (M + 1), 474 (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - phenyl) -methanol H-NMR (400 MHz, CD3OD) d (ppm) 7.62 (m, 3H) 7.50 (m, 4H) 7.35 (m, 3H) 7.20 (m, 1H) 4.50 (s, 2H) 2.73 (m, 1H) 2.52 (m, 1H) 1.95 (m, 1H) 1.78 (m, 1H). MS (ESI, pos. Ion) m / z: 409.1 (M + 1). 494 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. -phenyl) -propan-2-ol 1H-NMR (400 MHz , CD3OD) d (ppm) 7.83-7.86 (m, 1H) 7.44-7.49 (d, J = 8.08Hz, 1H) 7.34-7.40 (m, 2H) 7.14-7.28 (m, 3H) 7.12-7.18 (m, 2H) 3.80 (s, 3H) 2.60-2.65 (m, 1H) 2.31-2.35 (m, 1H) 1.78-1.82 (m, 1H) 1.62-1.70 (m, 1H) 1.34 (s, 6H). MS (ESI, pos. Ion) m / z: 399.1 (M + 1). 497 2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. -phenyl) -propan-2-ol H-NMR (400 MHz , DMSO d6) d (ppm) 12.30-12.40 (d, 1H) 7.84-7.87 (d, J = 7.83Hz, 1H) 7.45-7.48 (d, J = 7.83Hz, 1H) 7.29-7.40 (m, 6H) 7.17- 7.23 (m, 1H) 6.96-7.10 (m, 2H) 2.60-2.67 (m, 1H) 2.38-2.43 (m, 1H) 1.81-1.86 (m, 1H) 1.62-1.68 (m, 1H) 1.20 ( s, 6H). MS (ESI, pos. Ion) m / z: 453.3 (M + 1).
Comp. Name and data 498 2-. { 2- [2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1H-benzamidozol-5-yl} - benzamide H-NMR (400 MHz, DMSO d6) d (ppm) 12.5 (bs, 1 H) 7.68-7.72 (d, J = 8.08 Hz, 2H) 7.40-7.60 (m, 7H) 7.28 (s, 1 H ) 7.21-7.25 (dd, J = 1.77, 8.34Hz, 1 H) 2.70-2.78 (m, 1 H) 2.44-2.53 (m, 1 H) 1.90-1.99 (m, 1 H) 1.70-1.80 (m, 1 HOUR). MS (ESI, pos. Ion) m / z: 422.2 (M + 1). 499 N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl} 1-NMR-benzenesulfonamide (400 MHz, DMSO d6) d (ppm) 12.40 (s, 1 H) 8.2-8.3 (d, J = 9.34 Hz, 1 H) 7.30-7.70 (m, 9H) 7.10-7.15 (m , 1 H) 6.28-6.32 (m, 1 H) 2.64-2.72 (m, 1 H) 1.90-1.94 (m, 1 H) 1.70-1.75 (m, 1 H) 0.90 (s, 9H). MS (ESI, pos. Ion) m / z: 514.2 (M + 1). 500 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole 1H-NMR (400 MHz, DMSO d6) d (ppm) 8.12-8.15 (dd) , J = 1.26, 7.83Hz, 1 H) 7.70-7.83 (m, 6H) 7.53-7.57 (d, J = 8.08Hz, 2H) 7.42-7.47 (ddd, J = 1.26, 7.32Hz, 2H) 2.93-3.00 (m, 1 H) 2.66-2.74 (m, 1 H) 2.06-2.13 (m, 1 H) 1.97-2.03 (m, 1 H). MS (ESI, pos. Ion) m / z: 457.1 (M + 1).
PROPHETIC EXAMPLE 29 Through the procedures of Examples 27 or 28, and the reagents, starting materials and conditions known to those skilled in the art. art, the following representative prophetic compounds of the present invention can be prepared: Comp. Name and data 189 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - Benzenesulfonamide, 191 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 192 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide , 193 C, C, C-trifluoro-N- (2- {2 - [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 194 C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 195 1- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, Comp. Name and data 196 1- (2- { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 197 N- (2 - { 2- [2- (4-Chloro-pheny] -cyclopropyl] -1 H -benzyldazol-5-yl}. Phenyl) -methanesulfonamide, 2-. { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 200 N- (2-. {2- 2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) - CCC- trifluoro-methanesulfonamide, 201 1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzyldazol-5-yl.} - phenyl) -ethanone , 202 1 - (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, 203 N- (2 - { 2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. { 2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.] - phenyl) -propan-2-ol, 205 2-. - [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, 206 C, C, C-trifluoro-N- (2-. {2- 2- [ 2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 207 1- [2- (2-. {2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl] - 1 H-benzimidazol-5-yl) -phenyl] -ethanone, 208 1- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl.) - 1 H-benzimidazol-5-yl) -phenyl] -ethanol, 209 N- [2- (2-. { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 210 2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-tr Fluoromethyl-ethoxy) -phenyl] -cyclopropyl.] - 1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 211 2- (2-. {2- 2- (2, 2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -c-chloropropyl} -1 H -benzimidazol-5-yl) -benzenesulfonamide, 212 C, C, C-tr Fluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, 213 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzyldazole- 5-yl) -phenyl] -ethanone, 214 1- [2- (2- { 2- [4- (2,2,2-Trifluoro-ethoxy) -phenyl] -cyclopropyl}. -1 H-benzimidazol-5-yl) -phenyl] -ethanol, 215 N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) ) -pheny] -cyclopropyl] -1 H -benzamidazol-5-yl) -phenyl] -methanesulfonamide, 216 2- [2- (2-. {2- [4- (2,2,2-Trifluoro-ethoxy) -phenyl] -cyclopropyl] -1 H-benzyldazol-5-yl) -phenyl] -propan-2 -ol, 217 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl.] -1 H-benzimidazol-5-yl) -benzenesulfonamide , 218 C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl .) - H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, Comp. Name and data 219 1- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazole -5-yl) -phenyl] -ethanone, 220 1- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -c Chlorpropyl] -1 H- benzimidazol-5-yl) -phenyl] -ethanol, 221 N- [2- (2-. {2- 2- 4- (2,2,3,3,3 -pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 222 2- [2- (2-. {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 223 2- ( 2- {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl} -cyclopropyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, 224 C, , C-trifluoro-N- [2- (2-. {2- 2- [4- (2, 2,3,3, 3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1H-benzimidazole-5 -yl) -phenyl] -methanesulfonamide, 225 1- (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone , 226 1- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-N.}. -phenyl) -ethanol, 227 N- (2- { 2- [2- (3-chloro-phenyl) -cic lopropyl] -1H-benzimidazol-5-yl} phenyl) -methanesulfonamide, 228 2- (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol, 229 2-. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 230 N- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) - C, C, C-trifluoro methanesulfonamide, 231 1- (2-. {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -H-benzimidazol-5-yl.} - phenyl) -ethanone, 232 1 - (2- {. 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. -phenyl) -ethanol, 233 N- (2-. {2- 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 235 2-. { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 236 C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole -5-yl.}.-Phenyl) -methanesulfonamide, 237 N- (4-. {2- 2- [2- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl. phenyl) -methanesulfonamide, 238 N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, 239 N- (2-. {2- 2- [4 (methanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl). phenyl) -methanesulfonamide, 240 N- [4 - (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, 241 2- . { 2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, Comp. Name and data 242 C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1 H-benzimidazol-5-yl} -phenyl) -metanesulfonamide, 243 N- (4-. {2- 2- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl.} - phenyl) - C, C, C-trifluoro -methanesulfonamide, 244 C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -cyclopropyl) -phenyl] -methanesulfonamide, 245 C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl .}.-phenyl) -methanesulfonamide, 246 C, C) C-trifluoro-N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -fenN] -1 H- benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, 2-7. { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide and 248 C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -metansulfonamide.
EXAMPLE 30 2- [2- (2-Phenylethynyl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol (Compound 489) Step A.
(C) -5-bromo-2- (2-chloro-2-phenyl-vinyl) -1 H-benzimidazole A mixture of 4-bromo-benzene-1,2-diamine dihydrochloride (1.3 g, 5 mmol), phenylpropiolic acid (0.73 g, 5 mmol) in 4 ml of ethylene glycol was heated to reflux for 5 h. The mixture was cooled to rt and poured into Water. The mixture was neutralized with 2N sodium hydroxide and filtered. The solid is suspended in water and extracted with ethyl acetate. The organic phases are They were combined, dried with anhydrous sodium sulfate and filtered. The filtrate is concentrated to produce a red oil. The residue was purified twice by preparative TLC chromatography plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes 3: 7 and silica gel, 20 X 20 cm, 2000 microns, EtOAc: dichloromethane 3: 97) to provide a mixture of the cis and trans isomers of the title compound 30a (0.345 g). 1 H NMR (400 MHz, DMSO-d 6) d (ppm): 12.59 (m, 1 H), 7.86-7.78 (m, 3 H), 7.64-7.56 (m, 1 H), 7.54-7.49 (m, 3 H) , 7.46 (s, 1 H), 7.40-7.34 (m, 1 H). Mass spectrum (LCMS, APCI pos.) Calculated for C15H10BrCIN2: 333.0 (M + H), Experimental 333.1.
Step B 2-f2- (2-phenylethynyl-1H-benzimidazol-5-yl) -phenyl-propan-2-ol A mixture of Compound 30a (25 mg, 0.075 mmol), Compound 10e (18 mg, 0.113 mmol) and Pd (dppf) CI2CH2CI2 (12 mg, 0.015 mmoles) in 3 ml of DME and sodium carbonate solution (1.0 M, 0.6 ml) was heated at 150 ° C for 1 h in a Biotage Initiator ™ microwave synthesizer. The mixture was filtered through a pad of silica gel. The reaction was repeated three times in total. The residues were combined and purified twice in preparative TLC chromatography plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes 3: 7 and then silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes : methanol 2: 8: 1) to provide the title compound 489 (8.4 mg). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 7.78 (dd, 1 H, J = 8.1, 1.1 Hz, 1 H), 7.62-7.60 (m, 2 H), 7.52 (d, 1 H, J = 8.3 Hz), 7.46-7.38 (m, 4H), 7.31 (dt, 1 H, J = 1.5, 8.0 Hz), 7.21-7.17 (m, 2H), 7.02 (dd, J = 7.5, 1.3 Hz, 1 H) , 1.30 (s, 6H). Mass spectrum (LCMS, APCI pos.) Calculated for C24H20 2O: 353.2 (M + H), Experimental 353.3.
EXAMPLE 31 2- (2-Phenylethynyl-1 H-benzimidazol-5-yl) -benzenesulfonamide (Compound 490) Step A N-tert-butyl-2- (2-phenylethynyl-1H-benzimidazol-5-yl) -benzenesulfonamide A mixture of Compound 30a (25 mg, 0.075 mmol), 2- (tert-butylamino) sulfonylphenyl boronic acid (29 mg , 0.113 mmol), and Pd (dppf) CI2-CH2CI2 (12 mg, 0.015 mmol) in 3 ml of DME and sodium carbonate solution (1.0 M, 0.6 ml) was heated at 150 ° C for 1 h in a synthesizer Biotage Initiator ™. The mixture was filtered through a pad of silica gel. The residue was purified by preparative TLC (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes 3: 7) to give the title compound 31a (12.8 mg). Mass spectrum (LCMS, APCI pos.) Calculated for C25H23N3O2S: 430.2 (M + H), Experimental 430.3.
Step B 2- (2-Phenylethynyl-1 H-benzimidazol-5-yl) -benzenesulfonamide A mixture of Compound 31a (14.9 mg, 0.034 mmol) in trifluoroacetic acid and 1,2-dichloroethane (2 ml, 1: 1) was heated at 90 ° C for 3 h. The reaction was cooled to rt and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and the filtrate was removed under reduced pressure. The residue was purified by preparative TLC plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes: methanol 5: 5: 1) to give the title compound 490 (12.1 mg). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.1 1 (dd, 1 H, J = 8.0, 1.2 Hz), 7.67-7.56 (m, 5H), 7.52 (ddd, H, J = 7.6, 6.4, 1.4 Hz), 7.48-7.33 (m, 5H). Mass spectrum (LCMS, ESI pos.) Calculated for C2iH15N302S: 374.1 (M + H), Experimental 374.2. By the procedures described in Examples 30 and 31, and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared from the corresponding vinyl derivatives: Comp. Name and data 250 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamy 1 H NMR (400MHz, CD3OD) d (ppm): 8.04 (dd, 1 H, J = 8.0 , 1.2 Hz), 7.76 (d, J2H, = 8.2 Hz), 7.69 (d, 2H, J = 8.2 Hz), 7.58-7.53 (m, 2H), 7.54 (dt, 1 H, J = 1.4, 7.5 Hz ), 7.46 (dt, 1 H, J = 1.4, 7.7 Hz), 7.31 (dd, 1 H, J = 7.5, 1.3 Hz), 7.30 (dd, 1 H, J = 8.4, 0.9 Hz). Mass spectrum (LCMS, ESI pos.) Calculated for C22HHF3N3O2S: 442.1 (M + H), Experimental 442.2. 294 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol 1H NMR (400 MHz, CD3OD) d (ppm): 7.94 (s, 1 H), 7.89 (d, 1 H, J = 7.7 Hz), 7.80-7.74 (m, 2H), 7.66 (t, 1H, J = 7.8 Hz, 1 H), 7.60-7.39 (m, 2H), 7.33 (m, 1 H), 7.28-7.18 (m, 2H), 7.04 (dd, 1 H, J = 7.5 , 1.4 Hz, 1 H), 1.32 (s, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C25H19F3 20: 421.1 (M + H), Experimental 421.3. 295 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide 1 H NMR (400 MHz, CD3OD d (ppm): 8.11 (dd, 1 H, J = 8.0, 1.2 Hz ), 7.94 (s, 1 H), 7.89 (dm, 1 H, J = 7.6 Hz), 7.77 (dm, 1 H, J = 7.9 Hz), 7.67-7.58 (m, 4H), 7.52 (m, 1 H), 7.38 (dd, J = 7.5, 1.3 Hz, 1 H), 7.37 (br s, 1 H) Mass spectrum (LCMS, ESI pos.) Calculated for C22H1 F3N302S: 442.1 (M + H), Experimental 442.2 492 2- { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl.}. -propan-2-ol 1 H NMR (400 MHz, CD3OD) d ( ppm): 7.83 (d, 2H, J = 8.2 Hz), 7.79 (dd, 1 H, J = 8.2 1.1 Hz, 1 H), 7.76 (d, 2H, J = 8.3 Hz), 7.64-7.37 (m, 2H), 7.33 (m, 1 H), 7.22 (br d, 1 H, J = 7.2 Hz), 7.20 (dt, 1 H, J = 1.3, 7.4 Hz), 7.04 (dd, 1 H, J = 7.5 , 1.4 Hz), 1.32 (s, 6H) Mass Spectrum (LCMS, ESI pos.) Calculated for C ^ H ^ Fa ^ O: 421.1 (M + H), Experimental 421.3 Preparation of acid (4-trifluoromethylphenyl) propinoic To a solution of 4-ethynyl-a, a, α-trifluorotoluene (5 g, 29 mmol) in anhydrous THF ro (25 ml), 2.6M n-butylithium in hexanes (14.5 ml, 47 mmol) was slowly added. The mixture was stirred at -78 ° C for 30 min and then at 0 ° C for an additional 30 min. The mixture was cooled to -78 ° C and transferred through a cannula to a saturated solution of carbon dioxide in anhydrous THF (25 ml) at -78 ° C. The mixture was stirred and allowed to warm at rt for 18 h. The mixture was quenched by a saturated sodium chloride solution and the two phases were separated. The organic phase was washed with hexanes and then acidified with 2N hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and dried with anhydrous sodium sulfate and magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure to yield the title compound 31b as a white solid (5.4 g, 87%). H NMR (400MHz, DMSO-d6) d (ppm): 7.81 (s, 4H). Compound 31b was carried out by the procedure of Example 31 to provide the title compound 492.
PROPHETIC EXAMPLE 32 Through the procedures of Examples 30 or 31, the corresponding bromobenzimidazole and when it is not available in the market, the arylacetylene acid precursors prepared as describes in the KK Reaction Scheme and the reagents, starting materials and conditions known to those skilled in the art, the following representative prophetic compounds of the present invention.
Alternatively, the following compounds can be prepared from its corresponding vinyl compounds by hydrogenation: Comp. Name and data 249 2- [2- (4-trifluoromethoxy-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 251 2- [2- (4-trifluoromethanesulfonyl-phenylethynyl) -H-benzimidazol-5-yl ] -benzenesulfonamide, 252 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethoxy-phenylethynyl) -1 H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 253 C > C, C-trifluoro-N-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -H-benzimidazol-5-yl] -phenyl} -methanesulfonamide, 254 C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenylethynyl) -H-benzimidazol-5-yl] -phenyl} -methanesulfonamide, 255 1 -. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 256 1 -. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -ethanol, 257 N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -methanesulfonamide, 258 2-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 259 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 260 N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-trifluoro-methanesulfonamide, 261 1 -. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanone, Comp. Name and data 262 1 -. { 2- [2- (4-methanesulfonyl-phenletin) -1 H-benzimidazol-5-yl] -phenyl} -etanol, 263 N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -methanesulfonamide, 264 2-. { 2- [2- (4-methanesulfonyl-phenylethyl) -1 H -benzyldazol-5-yl] -phenyl} -propan-2-ol, 265 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5 i!] - benzenesulfonamide, 266 C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonyl-phen-ethyl-n-1) -1 H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 267 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethyl] -1 H-benzimidazole-5-one l.}.-phenyl] -ethanone, 268 1- (2- { 2- [4- (2,2,2-trifluoro-1-tr.fluoromethyl-ethoxy) -phenol. nl] -1 H-benzyldazol-5-yl.} - phenyl) -ethanol, 269 N- (2-. {2- 2- [4- (2,2,2-trifluoro-1 -trifluoromethyl-ethoxy!) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 270 2- (2-. {2- 2- [2- (2,2,2- trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 271 2-. { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 272 C, ClC-trifluoro-N- (2-. {2- 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1H-benzimidazole-5 -yl.}.-phenyl) -methanesulfonamide, 273 1- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethyl] -1 H- benzyl midazol-5-yl.}. phenyl) -ethanone, 274 1- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H- benzamidazole- 5-ii.) .phenyl) -ethanol, 275 N- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenolletyl] -1H-benzimidazole- 5-yl.}.-Phenyl) -methanesulfonamide, 276 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenethyl] -1 H- benzimidazol-5-yl.} - phenyl] -propan-2-ol, 277 2-. { 2- [4- (2,2,2-Trifluoro-ethoxy) -phenolletin] -1 H-benzimidazol-5-yl} -benzenesulfonamide, 278 C, C, C-trifluoro-N- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethyl] -1 H -benzamidazol-5-yl.} - phenyl) -methanesulfonamide, 279 1- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethanol] -1 H-benzimidazol-5-yl.}. -phenyl) -ethanone, 280 1- (2- { 2- [4- (2, 2,3,3, 3-pentafluoro-propoxy!) -phenylethynyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanol, 281 N- (2-. {2- 2- 4- (2,2,3,3 , 3-pentafluoro-propoxy) -phenylethyl] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 282 2- (2- { 2- [4- (2,2,3 , 3,3-pentafluoro-propoxy!) -phenylethynyl] -1H-benzyldazol-5-yl.} - phenyl) -propan-2-ol, 283 2-. { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethyl] -1 H- benzimidazol-5-yl} -benzenesulfonamide, Comp. Name and data 284 C, C, C-trifluoro-N- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxyJ-phenyletinyl-I H-benzimidazole-S -ilHeni-methanesulfonamide, 285 1 -. { 2- [2- (3-Chloro-phenylethyl) -1 H -benzimidazol-5-yl] -phenyl-ethanone, 286 2-. { 2- [2- (3-Chloro-phenylethenyl) -1 H -benzyldazol-5-yl] -phenol} -propan-2-ol, 287 N-. { 2- [2- (3-Chloro-phenylethyl) -1 H-benzimidazol-5-yl] -phenyl-methanesulfonamide, 288 1-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -ethanol, 289 2- [2- (3-chloro-phenylethyl] -1 H-benzimidazol-5-yl] -benzenesulfonamide, 290 N-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-trifluoro-methanesulfonamide, 291 1-. { 2- [2- (3-trifluoromethyl-phenylethyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 292 1 -. { 2- [2- (3-trifluoromethyl-phenletin) -1 H-benzimidazol-5-yl] -phenyl} -etanol, 293 N-. { 2- [2- (3-Trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 296 C, C, C-trifluoro-N-. { 2- [2- (3-trifluoromethyl-phenletin) -1 H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 297 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl-methanesulfonamide, 298 N- (4-. {5- [2- (1-hydroxy) ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl}. phenyl) -methanesulfonamide, 299 N-. { 2- [2- (4-methanesulfonylamino) -phenylethyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 300 N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl} .-phenyl) -metanesulfonamide, 301 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 302 C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H-benzimidazol-5-yl] -phenyl} -metansulfonamida, 303 N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -C, C, C-trifluoro-methanesulfonamide, 304 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H- benzimidazol-2-yl-ethyl}. phenyl) -methanesulfonamide, 305 C, C, C-trifluoro-N-. { 4- [5- (2-methanesulfonylamino-pheny] - 1 H -benzimidazol-2-yl-ethynyl] -phenyl} -metanesulfonamide, 306 C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzyl midazol-2-yl-ethynyl}. phenyl) -methanesulfonamide, 307 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide and Comp. Name and data 0,0,0-? P? 1 ?? G? -? -. { 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzim-methanesulfonamide.
EXAMPLE 33 (-2- ^ 2-r2- (2 ^ uinolin-6-yl-vinyl) -1 H -benzimidazole-5-in-phenyl) -propan-2-ol (Comp .. 449) Step A 5-bromo-2-chloromethyl-1 H-benzimidazole A mixture of 4-bromo-benzene-1,2-dinamine (200 mg, 1.07 mmoles) and the hydrochloride salt of the ethyl ester of 2-chloroacetymidic acid (168 mg, 1. 07 mmoles; prepared according to the procedure described in J.
Med. Chem. 1986, 29, 2280) in anhydrous ethanol (100%, 5 ml) was stirred room temperature for 4 h. The reaction mixture was concentrated to reduced pressure and extracted with ethyl acetate and water. The organic phase dried with Na2SO4, filtered and the filtrate was concentrated in vacuo to provide the compound of title 33a as a white solid (240 mg, 92% performance). 1 H NMR (400MHz, CDCl 3) d (ppm): 7.75 (d, 1 H, J = 1.4Hz), 7.47 (d, 1 H, J = 8.6Hz), 7.42 (dd, 1 H, J = 8.6Hz, J = 1.3Hz), 4.84 (s, 2H).
Mass spectrum (LCMS, ESI pos.) Calculated for C18H2oCIN302S: 247.50 (M + H), Experimental 247.0.
Step B (5-Bromo-1 H-benzimidazol-2-ylmethyl) -triphenyl-phosphonium chloride A mixture of Compound 33a (240 mg, 0.98 mmol) and triphenylphosphine (385 mg, 1.47 mmol), in 1,2-dichloroethane (10 mi) was heated at 140 ° C for 1 h. The reaction mixture was concentrated under reduced pressure to provide the title compound 33b, which was used in the next step without further purification.
Step C (E) -6- [2- (5-Bromo-1 H-benzimidazol-2-yl) -vinill-quinoline A mixture of Compound 33b (100 mg, 0.204 mmol), 6-quinolinecarboxaldehyde (32 mg, 0.29 mmol) and DBU (39.6 ul, 0.265 mmole) in ethanol: tetrahydrofuran (1: 1, 2 ml) was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by reverse phase preparative HOLC (10-100% acetonitrile / water gradient for 10 min) to give the title compound 33c as a white solid (50 mg, 72 mg). % of performance). Calculated for Ci8Hi2BrN3: 350.21 (M + H), Experimental 350.2.
Step D (E) -2- (2- [2- (2-quinolin-6-yl-vinyl) -1H-benzimidazole-5-in-phenyl-1-propan-2-ol A mixture of Compound 33c (50.0 mg, 0.143 mmol) , Compound 10e (46 mg, 0.29 mmol), PdCI2 (dppf) (23.4 mg, 0.029 mmol) and 1M sodium bicarbonate solution (1.15 mL, 1.15 mmol) in 1,2-dimethoxyethane (1 mL) was heated to reflux for 12 h . The reaction mixture was concentrated under reduced pressure, the residue was purified by chromatography (silica, EtOAc) to give the title compound 449 as a white solid (11.8 mg, 20% yield). H NMR (400MHz, CD3OD) d (ppm): 9.01 (br s, 1 H), 8.68 (d, 1 H, J = 8.1 Hz), 8.35 (m, 2H), 8.12-8.21 (m, 2H), 7.76 (m, 3H), 7.67 (s, 1H), 7.53 (m, 2H), 7.38-7.43 (m, 1 H), 7.28 (m, 1 H), 7.09 (m, 1 H), 1.42 (s) , 6H). Calculated for C ^ H ^ NaO: 406.5 (M + H), Experimental 406.3. By the procedures described in Example 33 and reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 448 (£) -1 - [4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. vinyl) -phenyl] -ethanone The title compound was prepared from Compound 33b (100 mg, 0.204 mmol) and 4-acetylbenzaldehyde (30.2 mg, 0.204 mmol) as a white solid (3.75 mg, 10% yield) . 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.06 (d, 1 H, J = 8.8 Hz), 7.96 (m, 1 H), 7.80 (m, 3 H), 7.68 (m, 1 H), 7.55 ( m, 1 H), 7.43 (m, 1 H), 7.34 (m, 2H), 7.17-7.24 (m, 2H), 7.07 (m, 1 H), 2.63 (s, 3H), 1.35 (s, 6H) ). Mass spectrum (LCMS, ESI pos.) Calculated for C ^ H ^ N; ^: 397.5 (M + H), Experimental 397.3. 450 (£) -N-isopropyl-4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} -benzamide The title compound was prepared from Compound 33c [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-ylmethyl] -triphenyl-phosphonium chloride (90 mg, 0.15 mmol) and 4-carboxyaldehyde -N-isopropylbenzamide (24.3 mg, 0.15 mmol) as a white solid (10.5 mg, 15% yield). 1 H NMR (400MHz, CD 3 OD) d (ppm): 8.06 (dd, 1 H, J = 8.1, Hz, J = 1.5Hz), 7.87 (m, 2H), 7.55-7.74 (m, 7H), 7.43 (dd) , 1 H, J = 8.1 Hz, J = 1.5 Hz), 7.29 (m, 2 H), 4.22 (m, 1 H), 2.37 (s, 3 H), 1.26 (s, 6 H). Mass spectrum (LCMS, ESI pos.) Calculated for C ^ H ^ OaS: 475.5 (M + H), Experimental 475.2. 451 (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methylbenzenesulfonamide The title compound was prepared from Compound 33c (90 mg, 0.15 mmol) and 4-cyanobenzaldehyde (19.6 mg, 0.15 mmol) as a white solid (7.4 mg, 12% yield). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.07 (dd, 1 H, J = 8.0 Hz, J = 1.0 Hz), 7.49-7.69 (m 8 H), 7.37 (m, 2 H), 7.20 (m, 2H), 2.32 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H18N402S: 415.5 (M + H), Experimental 415.2. 452 (E) -N- (4-. {2- 2- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) -acetamide The title compound is prepared from Compound 33c (90 mg, 0.15 mmol) and 4-acetamidobenzaldehyde (24.3 mg, 0.15 mmol) as a white solid (1.3 mg, 17% yield). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.04 (dd, 1 H, J = 8.0 Hz, J = 1.3 Hz), 7.63 (td, 1 H, J = 7.4 Hz, J = 1.4 Hz), 7.55 ( m, 5H), 7.26-7.39 (m, 5H), 7.19 (dd, 1 H, J = 8.1 Hz, J = 1.5Hz), 2.22 (s, 3H), 2.03 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H22N4O3S: 447.5 (M + H), Experimental 447.2. 453 Acid (E) -4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl-benzoic The title compound was prepared from Compound 33c (90 mg, 0.15 mmol) and 4-carboxybenzaldehyde (22.4 mg, 0.15 mmol) as a white solid (3.4 mg, 5% yield). H NMR (400MHz, CD3OD) d (ppm): 8.02 (m, 2H), 7.53-7.77 (m, 6H), 7.18-7.45 (m, 5H), 2.36 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C23H19N304S: 434.5 (M + H), Experimental 434.2.
Comp. Name and data 454 (E) -2-. { 2- [2- (1 H-indol-6-yl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide The title compound was prepared from Compound 33c (90 mg, 0.15 mmole) and indole-6-carboxaldehyde (21.6 mg, 0.15 mmole) as a white solid (6.5 mg, 10% yield). 1 H NMR (400MHz, CD 3 OD) d (ppm): 8.06 (m, 1 H), 7.05-7.73 (m, 1 1 H), 6.48 (m, 2H), 2.36 (m, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H20N4O2S: 429.5 (M + H), Experimental 429.2. 455 (£) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - N-methyl-benzenesulfonamide The title compound was prepared from Compound 33c (90 mg, 0.15 mmol) and 2,4-bis (trifluoromethyl) benzaldehyde (24.4 uL, 0.15 mmol) as a white solid (8.62 mg, 11%). of performance). 1 H NMR (400MHz, CD 3 OD) d (ppm): 7.14-8.17 (m, 12H), 2.44 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H17F6N302S: 526.5 (M + H), Experimental 526.3. 456 (E) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide The title compound was prepared from Compound 33c (90 mg, 0.15 mmol) and 4-acetylbenzaldehyde (22.1 mg, 0.15 mmol) as a white solid (8.32 mg, 13% yield). H NMR (400MHz, CD3OD) d (ppm): 8.06 (m, 3H), 7.56-7.79 (m, 9H), 7.44 (m, 1 H), 2.62 (s, 3H), 2.37 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C24H21N303S: 432.5 (M + H), Experimental 432.2.
EXAMPLE 34 2 ^ 2- [2- (4-trifluoromethyl-phenyl) -etin-1H-benzimidazol-5-yl > -bencilam¡na fComp. 486) Step A (a-2- (2-f2- (4-trifluoromethyl-phenyl-vinyl-1-H-benzimidazol-5-yl) -benzonitrile A mixture of Compound 10c (52 mg, 0.14 mmol), 2-cyanophenylboronic acid (38 mg, 0.26 mmol), Pd (dppf) CI2CH2CI2 (36 mg, 0.044 mmol), tetrabutylammonium bromide (55 mg, 0.17 mmol), and Sodium carbonate (1 mL, 1.0 M) in DME (5 mL) was heated at 90 ° C for 18 h. The mixture was cooled to rt, filtered through a pad of celite and concentrated under reduced pressure. The residue was purified by preparative TLC plates (silica gel, 20 X 20 cm, 2000 microns, EtOAc: hexanes 1: 1 and hexanes: dichloromethane: methanol 6: 14: 1) to provide the title compound 34a (20 mg , 37%). 1 H NMR (400 MHz, CD 3 OD + CDCl 3) d (ppm): 7.72-7.47 (m, 10 H), 7.40-7.30 (m, 3 H), 7.14 (d, 1 H, J = 16.55 Hz). Mass spectrum (LCMS, APCI pos.) Calculated for C23Hi4F3N3 :, 390.1 (M + H), Experimental 390.3.
Step B 2-f2-r2- (4-Trifluoromethyl-phenyl) -etin-1 H-benzimidazol-5-yl) -benzylamine A mixture of Compound 34a (20 mg, 0.051 mmol), Raney®-Nickel, ammonium hydroxide (0.1 ml) in ethanol was hydrogenated at 344.5 kPa (50 psi) for 18 h. The mixture was filtered through a pad of celite and washed with ethanol. The filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC plates (silica gel, 20 X 20 cm, 2000 microns, NH 3 in methanol: EtOAc 1: 9) to give the title compound 486 (6.3 mg, 31%). 1 H NMR (400 MHz, CD 3 OD) d (ppm): 7.57-7.52 (m, 4H), 7.46-7.34 (m, 6H), 7.14 (dd, J = 8.2, 1.5 Hz, 1 H), 4.05 (s, 2H), 3.24 (s, 4H). Mass spectrum (LCMS, APCI pos.) Calculated for C23H20F3 3: 396.2 (M + H), Experimental 396.2.
EXAMPLE 35 Z) -2- (2- | 2-r2- (4-Trifluoromethyl-phenyl) -vinin-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol (Compound 469) A solution of Compound 18 (0.030 g, 0.07 mmol) in DMSO (5 mL) was stirred at room temperature for 5 days with a 60W lamp. The reaction was then applied to 2000 microns of a preparative TLC plate (20 X 20 cm) and developed by 4: 6 ethyl acetate: hexanes. The desired band was extracted with MeOH, filtered and concentrated to provide the title compound 469 (0.001 g). 1 H-NMR (400 MHz, DMSO d 6) d (ppm) 7.71 (dd, J = 1.01, 8.34 Hz, 1 H) 7.53 (s, 4 H) 7.37-7.41 (m, 1 H) 7.21-7.28 (m, 2H ) 7.1 1 (dt, J = 1.26, 7.33Hz, 1 H) 7.05 (dd, J = 1.52, 8.34Hz, 1 H), 6.94-7.10 (m, 4H) 6.67 (d, 12.6Hz, 1 H) 1.23 (s, 6H). MS (ESI, pos. Ion) m / z: 423.2 (M + 1).
EXAMPLE 36 (-N- (2- ^ 3-methyl-2-f2- (4-trifluoromethyl-phenyl) -vinyl-3H-benzimidazol-5-yl) -pheni-methanesulfonamide (Compound 443) (E) -N- (2- { 1-methyl-2-y2- (4-trifluoromethyl-phenyl) -vinyl-1 H-benzimidazol-5-yl) -phenyl) -methanesulfonamide (Compound 477) Step A (E) -5-bromo-1-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazole and (E-6-bromo-1-methyl-2-f2- (4-trifluoromethyl) phenyl) -vinin-1 H-benzimidazole To a solution of sodium hydride (suspension 60% in oil, 0.131 g, 3.2 mmol) in anhydrous tetrahydrofuran (10 mL) was added Compound 10c (1 g, 2.7 mmol). The solution was stirred at room temperature under an argon atmosphere, After five minutes, methyl iodide (0.205 ml, 3.2 mmol) was added and the solution was stirred at room temperature for 3 hrs. ethyl (10 ml) and ice water (20 ml) The organic fraction was washed with brine, dried with magnesium sulfate, then filtered and concentrated to provide a 1: 1 mixture of the title compound 36a and 36b (0.38 g). g).
Step B (aN- (2- (3-methy) -2-y2- (4-trifluoromethyl-phenyl) -vinyl-3H-benzimidazol-5-yl) -phenyl) -methanesulfonamide and (E) -N- (2 - { 1-methyl-2- [2- (4-trifluoromethyl-pheny] -vinin-1 H-benzimidazol-5-yl-phenyl) -methanesulfonamide. By the procedure of Example 1, Step B, the title compounds were prepared from a mixture of (£) -5-bromo-1-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole and (E) -6-bromo-1- methyl-2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazole and 2-methylsulfonylaminophenyl boronic acid. Comp. 443: 1 H-NMR (400 MHz, CD3OD) 5 (ppm) 7.82-7.80 (m, 3H) 7.75 (d, J = 8.1 Hz, 3H) 7.52-7.62 (m, 3H) 7.34-7.42 (m, 4H) 4.00 (s, 3H) 2.76 ( s, 3H). MS (ESI, pos. Ion) m / z: 472.1 (M + 1). Comp. 477: 1H-NMR (400 MHz, CD3OD) 5 (ppm) 7.88-7.95 (m, 3H) 7.72-7.77 (m, 3H) 7.56-7.67 (m, 4H) 7.40-7.44 (m, 3H) 4.10 (s) , 3H) 2.73 (s, 3H). MS (ESI, pos. Ion) m / z: 472.1 (M + 1).
EXAMPLE 37 (α-2-Hydroxy-1- (2 ^ 2 2- (4-trifluoromethyl-phenyl) -vinin-1H-benzimidazol-5-ylV-phenylH-ethanone (Compound 311) Step A (£) -2- [2- (4-rifluoromethyl-phenyl) -vinill-5- [2- (1-trimethylsilanyloxy-vinyl) -fenifl-1 H-benzimidazole To a solution of Compound 15 (0.20 g, 0.492 mmoles) in 16 mL of 1,2-dichloroethane was added TBSOTf (0.19 mL, 1.08 mmol) and Et3N (0.27 mL, 1.97 mmol) at 0 ° C. After 5 min., The mixture was heated to 25 ° C and stirred for 8 hours. The reaction was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 4: 1) to give the title compound 37a as a colorless oil.
Step B (-2-r2- (4-trifluoromethyl-phenyl) -vinill-5-r2- (2-trimethylsilanyloxy-oxiranyl) -phenyl-1 H-benzimidazole A mixture of Compound 37a (0.124 g, 0.238 mmol) and mCPBA (0.053 g, 0.238 mmol) in 10 mL of CH2Cl2 was stirred for two hours.The reaction was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 4: 1) to give the title compound 37b as a yellow oil Step C.
(E) -2-hydroxy-1- (2. {2-r2- (4-trifluoromethyl-phenyl) -vinn-1 H-benzimidazol-5-yl) -phenyl) -ethanone A mixture of the Compound 37b (0.026 g, 0.048 mmol) and p-toluenesulfonic acid monohydrate (p-TsOHH2O, 0.018 g, 0.0968 mmol) in 4 mL of THF was stirred for four hours. The reaction was concentrated and the residue was purified by chromatography (silica gel, hexanes: EtOAc, 1: 2) to give the title compound 311 as a brown solid. 1 H-NMR (400 MHz, CD 3 OD) d (ppm): 7.85 (d, 2 H, J = 8.8 Hz) 7.74 (d, 2 H, J = 7.6 Hz) 7.71 (d, 1 H, J = 16.4 Hz) 7.63- 7.47 (m, 6H) 7.33 (d, 1 H, J = 16.0 Hz) 7.25 (dd, 1 H, J = 1.6 and 8.4 Hz) 4.08 (s, 2H) MS (ESI, pos. Ion) m / z: 423.3 (M + 1).
EXAMPLE 38 2- (2 2-r (1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl-1H-benzimidazol-5-yl) -phenyl) -propan-2-ol (Comp. 501) Step A (1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid ethyl ester A suspension of the copper trifluoromethanesulfonate (l) -toluene complex (31.0 mg, 0.12 mmol) in anhydrous CHCl3 (3.0 ml) is added a solution of 2,2-bis - [(4S) - (1,1-dimethylethyl) -1,3-oxazolin-2-yl] propane (35 mg, 0.12 mmol) in chloroform (1.2 ml). After stirring at room temperature for 1 h, the resulting green solution was filtered through glass wool under argon atmosphere in a flask previously charged with a solution of 4- (trifluoromethyl) -styrene (0.887 ml, 6.00 mmol) in chloroform (0.9 ml). To this solution was added a solution of ethyl diazoacetate (1.56 ml, 15.0 mmol) in chloroform (12.0 ml) at room temperature via an addition funnel over a period of 6 h. The resulting mixture was stirred for 24 h, concentrated to dryness and purified by flash column chromatography on silica gel (silica gel 45 mm X 140 mm), eluting with ethyl acetate / hexane (1, 1.5, 2% ) to provide the title compound 38a (892 mg, 58% yield, 98% ee) as a colorless liquid and cis isomer of Compound 38b, (1 R.2S) -2- (4-trifluoromethyl) ethyl ester l-phenyl) -cyclopropanecarboxylic acid (128 mg, 5% yield calculated on the basis of 34% by weight of ethyl fumarate contamination analyzed by 1 RMN). The enantiomeric excess of the product was determined as described in the following Step E H-NMR of Compound 38a (400 MHz, CDCl 3) d (ppm): 7.53 (d, 2H, J = 8.3 Hz), 7.23 (d, 2 H, J = 8.1 Hz), 4.18 (q, 2 H, J = 7.1 Hz), 2.55 (dd, 1 H, J = 2.6, 4.3, &6.6 Hz), 1.94 (ddd, 1 H, J = 4.3, 5.6, &9.6 Hz), 1.68-1.53 (m, 1 H), 1.34 (1 H, ddd, 4.8, 6.7, &1.1 Hz), 1.29 (t, 2H, J = 7.0 Hz). 1 H-NMR of Compound 38b (400 MHz, CDCl 3) d (ppm): 7.51 (d, 2H, J = 7.9 Hz), 7.37 (d, 2H, J = 7.8 Hz), 3.92-3.86 (m, 2H), 2.62-2.56 (m, 1 H), 2.14 (ddd, 1 H, J = 5.8, 8.1 &9.3 Hz), 1.73 (td, 1 H, J = 5.3 & 7.6 Hz), 1.39 (ddd, 1 H , J = 5.1, 7.8 &8.6 Hz), 0.99 (t, 3H, J = 7.1 Hz).
Step B Acid (1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid To a solution of Compound 38a (750 mg, 2.91 mmol) in ethanol (7.27 ml) was added a 1 M aqueous solution of NaOH (7.27 ml). The resulting mixture was stirred at room temperature for 16 h, concentrated to about 4 g, acidified with 2M HCl to pH 3, and extracted with ethyl acetate (15 ml x 2). The extracts were combined, washed with brine, dried with Na 2 SO 4), concentrated to give the title compound 38c (61 mg, 91% yield) as a white solid. 1 H NMR (400 MHz, CDCl 3 with a drop of CD 3OD) d (ppm): 7.51 (d, 2H, J = 8.3 Hz), 7.18 (d, 2H, J = 8.1 Hz), 2.57 (ddd, 1 H, J = 4.2, 6.6, & 10.3 Hz), 1.90 (ddd, 1 H, J = 4.0, 5.3, &8.3 Hz), 1.65 (dt, 1 H, J = 4.9 &9.3 Hz), 1.35 (ddd, 1 H, J = 4.9, 6.4, &1.1 Hz).
Step C: 2- (2- {2-i (1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyn-1 H-benzimidazol-5-yl) -phenyl) -propan-2-ol By the procedure of Example 10, Steps B and E, the title compound 501 was prepared from Compound 38c. H-NMR (400 MHz, DMSO-d6)? (ppm): 12.40 (s, 0.5 H), 12.32 (s, 0.5 H), 7.87-7.84 (m, 1 H), 7.66 (d, 2H, J = 8.0 Hz), 7.49-7.17 (m, 6H) , 7.00-6.96 (m, 2H), 4.84 (s, 1 H), 2.72-2.67 (m, 1 H), 2.50-2.46 (m, 1 H), 1.92-1.86 (m, 1 H), 1.74- 1.68 (m, 1 H), 1.19 (s, 3H), 1.18 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C26H24F3N2O: 437.2. Experimental 437.3.
Step D: methoxy-methyl-amide of (1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid To a mixture of Compound 38c (50 mg, 0.216 mmol),?,? -dimethylhydroxylamine hydrochloride (30 mg, 0.30 mmol), BOP (134 mg, 0.30 mmol), and DMF (0.4 mL) was added DIEA (0.15 mL). The resulting mixture was stirred at room temperature for 48 h, concentrated to dryness and partitioned between saturated NaHCO3 (2 mL) and ethyl acetate (40 mL). The ethyl acetate layer was separated and the aqueous phase was extracted with ethyl acetate (5 ml X 2). All the ethyl acetate layers were combined, washed with brine, dried with Na 2 SO 4, concentrated and purified by preparative TLC, developed with 10% ethyl acetate / DCM to provide Compound 38d (46 mg, 78% of performance) as a white solid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 7.52 (d, 2 H, J = 8.4 Hz), 7. 23 (d, 2H, J = 8.1 Hz), 3.70 (s, 3H), 3.24 (s, 3H), 2.56-2.52 (m, H), 2.45 (bs, 1 H), 2.17-1.67 (m, 1 H), 1.34 (ddd, 1 H, J = 4.6, 6.3, &8.7 Hz).
Step E Determination of ee: To a solution of Compound 38d (0.8 mg) in CDCl 3 (0.6 ml) was added portion to portion (R) - (-) - 2,2,2-trifluoro-1- (9-anthryl) ethanol and the amount of addition was controlled by 1HRMN until the baseline resolution of the methoxy singlet was reached. Thus, the methoxy singlets of the enantiomer were around 3.47 and 3.45 ppm. The integration of these singlet was 99 and 1, respectively; in this way an ee value of 99% was obtained. Using the procedure described in Example 38 and the reagents, starting materials and conditions known to those skilled in the art, the following representative compounds of the present invention were prepared: Comp. Name and data 502 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl) -1) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide By the procedure of Example 38, the title compound was prepared from Compound 38c and 2- (t-butylamino) sulfonylphenyl boronic acid. 1 H-NMR (400 MHz, CDCl 3) d (ppm): 12.42 (s, 0.5H), 12.40 (s, 0.5H), 8.04 (dd, 1 H, J = 1.3 &7.8 Hz), 7.66 (d, 2H, J = 8.3 Hz), 7.63-7.34 (m, 7H), 7.17-7.11 (m, 1 H), 7.06 (s, 1 H), 7.03 (s, 1 H), 2.71-2.65 (m, 1 H), 2.50-2.46 (m, 1 H), 1.92-1.87 (m, 1 H), 1.75-1.70 (m, 1 H). Mass spectrum (LCMS, ESI pos.) Calculated for C23Hi9F3 302S: 458.1 (M + 1). Experimental 458.2. 503 monosodium salt of 2- (2- {2 - [(1 S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) - propan-2-ol Using the procedure of Example 38, the title compound was prepared from 2.2-bis - [(4R) - (1,1-dimethylethyl) -. 3-oxazolin-2-yl] propane and 4- ( trifluoromethyl) -styrene. To a suspension of N, N'-bis - [(2R) -3,3-dimethyl-1-hydroxybutyl] -2,2-dimethyl-1,3-propanediamide (83 mg, 0.25 mmol, prepared according to the procedure described in J. Am. (Cf. Soc. 1991, 113, 726) in DCM (2.5 ml), (diethylamino) sulfur trifluoride (0.066 ml, 0.50 mmol, as described in J. Org. Chem. 2002, 67, was added dropwise). 8566 for the formation of oxazoline from hydroxyamide) at room temperature. The resulting mixture was stirred at room temperature for 16 h and poured into saturated NaHCO3 (4.0 mL). The mixture was extracted with DCM (3 x 5 mL). The extracts were combined and dried with a2SÜ, then concentrated and subjected to flash chromatography with ethyl acetate / DCM (0, 5, 10, and 20%) to give 2.2-bis- [2 - ((4R) - (1,1-D-methylethyl) -1,3-oxazolinyl)] propane (53 mg, 72% yield) as a white solid. H-NMR was identical to that reported in the literature by Evans. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 7.82 (dd, 1 H, J = 1.5 &; 8.1 Hz), 7.61 (d, 2H, J = 8.1 Hz), 7.37 (d, 2H, J = 8.1 Hz), 7.24 (dt, 1 H, J = 1 .8 &7.3 Hz), 7.15-7.11 ( m, 2H), 7.00 (d, 1 H, J = 1.5 Hz), 6.98 (dd, 1 H, J = 1.5 &7.3 Hz), 6.52 (d, 1 H, J = 7.8 Hz), 4.63 (bs , 1 H), 2.52-2.47 (m, 1 H), 2.33 (ddd, 1 H, J = 4.1, 5.8 &8.8 Hz), 1.75 (ddd, 1 H, J = 3.7, 5.8, &8.8 Hz ), 1.45-1.40 (m, 1 H), 1.22 (s, 6H). Mass spectrum (LCMS, ESI pos.) Calculated for C26H24F3 20: 437.2. Experimental 437.2. In a manner analogous to Example 38, step A, both the trans isomer of Compound 38e, (1S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid ethyl ester and the cis isomer of Compound 38f were isolated, (1 S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid ethyl ester.
Comp. Name and data 504 2-. { 2 - [(1S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclochlor] -1 H -benzimidazol-5-yl} -benzenesulfonamide Using the procedure described for Compound 503, the title compound was prepared from Compound 38e, 4- (trifluoromethyl) -styrene and 2- (t-butylamino) sulfonylphenyl boronic acid. 1 H-NMR (400 MHz, DMSO-d 6) d (ppm): 12.41 (s, 0.5H), 12.40 (s, 0.5H), 8.04 (dd, 1 H, J = 1.3 &7.8 Hz), 7.66 ( d, 2H, J = 8.3 Hz), 7.63-7.34 (m, 7H), 7.17-7.1 1 (m, 1 H), 7.06 (s, 1 H), 7.03 (s, 1 H), 2.71 -2.65 ( m, 1 H), 2.50-2.46 (m, 1 H), 1.92-1.87 (m, 1 H), 1.75-1.70 (m, 1 H). MS (ESI, pos. Ion) m / z: 458.2 (M + 1). Mass spectrum (LCMS, ESI pos.) Calculated for C23H19F3 302S: 458.1 (M + 1). Experimental 458.2. 505 2- (2- {2 - [(1S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- By the procedure described for Compound 503, the title compound was prepared from Compound 38f. 1 H-NMR (400 MHz, CD3OD) d (ppm): 7.79 (dd, 1 H, J = 1.0 &8.1 Hz), 7.36-7.15 (m, 8H), 7.01 (t, 1 H, J = 1.5 Hz), 6.99 (d, 1 H, J = 1.5 Hz), 2.83-2.73 (m, 2H), 2.08-2.03 (m, 1 H), 1.71 (td, 1 H, J = 8.6 & 5.6 Hz) , 1.23 (s, 3H), 1.22 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C26H24F3N2O: 437.2. Experimental 437.3. Determination of ee: To a mixture of (1 S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid (14 mg, 0.0.061 mmol), (S) - (-) - a-methylbenzylamine (10.0) mg, 0.0609 mmol), BOP (27 mg, 0.0609 mmol), and DMF (0.2 mL) was added DIEA (0.023 mL, 0.13 mmol). The resulting solution was stirred at room temperature for 48 h, concentrated to dryness and partitioned between saturated NaHCO 3 (1 mL) and ethyl acetate (3 mL). The ethyl acetate layer was separated and the aqueous phase was extracted with ethyl acetate (5 ml X 2). All the ethyl acetate layers were combined, washed with brine, dried with Na 2 SO 4, concentrated and purified by preparative TLC, developed with 10% ethyl acetate / DCM to give the title compound (10.1 mg, 70%). % yield) as a white solid. 1 H-NMR (400 MHz, C6D6) d (ppm): 7.26 (d, 2H, J = 8.1 Hz), 7.03-6.95 (m, 5H), 6.68-6.65 (m, 2H), 4.96-4.89 (m , 1 H), 4.79 (bd, 1 H, J = 7.6 Hz), 1.80-1.73 (m, 2H), 1.23-1.17 (m, 1 H), 1.00 (d, 3H, J = 6.8 Hz), 0.82 -0.79 (m, 1 H). ). The 1 H-NMR double of Me (1 R, 2 S, 1 S) -N- (1'-phenethyl) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxamide appeared at 0.85 ppm. The integration of this double of methyl and that of the compound of the title was 2.5 and 97.5, respectively. 506 2-. { 2 - [(1 R, 2 S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide By the procedure of Example 38, the title compound was prepared from Compound 38b and 2- (t-butylamino) sulfonylphenyl boronic acid. 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.09 (dd, 1 H, J = 1.3 &7.9 Hz), 7.59 (dt, 1 H, J = 1.6 &7.6 Hz), 7.51 (dt , 1 H, J = 1.5 &7.8 Hz), 7.47 (bs, 1 H), 7.42-7.29 (m, 6H), 7.19 (dd, 1 H, J = 1.7 &8.3 Hz), 2.84-2.74 ( m, 2H), 2.05 (q, 1 H, J = 6.3 Hz), 1.72 (td, 1 H, J = 8.5 &5.7 Hz). Mass spectrum (LCMS, ESI pos.) Calculated for C23H19F3N3O2S: 458.1 (M + 1). Experimental 458.2. 507 2- (2- {2 - [(1 R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 - ol Using the procedure of Example 38, the title compound was prepared by Compound 38b. 1 H-NMR (400 MHz, CD3OD) d (ppm): 7.79 (dd, 1 H, J = 1.0 &8.1 Hz), 7.36-7.15 (m, 8H), 7.01 (t, 1 H, J = 1.5 Hz), 6.99 (d, 1 H, J = 1.5 Hz), 2.83-2.73 (m, 2H), 2.08-2.03 (m, 1 H), 1.71 (td, 1 H, J = 8.6 & 5.6 Hz) , 1.23 (s, 3H), 1.22 (s, 3H). Mass spectrum (LCMS, ESI pos.) Calculated for C26H24F3N2O: 437.2. Experimental 437.3. Determination of ee: Using the procedure described for Compound 506, the amide dimetidiary of Compound 507 was prepared from Compound 38g, (1 R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxylic acid and (S) ) - (-) - a-methylbenzylamine. 1 H-NMR (400 MHz, C6D6) d (ppm): 7.37 (d, 2H, J = 8.1 Hz), 7.35-7.02 (m, 5H), 6.97-6.95 (m, 2H), 4.95-4.88 (m , 1 H), 4.82 (bd, 1 H, J = 7.8 Hz), 1.81 -1.75 (m, 1 H), 1.70 (ddd, 1 H, J = 4.8, 5.8 &; 7.3 Hz), 1.14 (ddd, 1 H, J = 5.6, 7.8 &9.0 Hz), 0.85 (d, 3H, J = 6.6 Hz), 0.80-0.75 (m, 1 H). At 1 H-NMR the doublet of Me in (1S, 2R, rS) -N- (1'-phenethyl) -2- (4-trifluoromethyl-phenyl) -cyclopropanecarboxamide appeared at 1.00 ppm. The integration of this methyl double and that of the title compound was 3 and 97, respectively.
Comp. Name and data 508 2-. { 2 - [(1 S, 2R) -2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide By the procedure described for Compound 503, the title compound was prepared from Compound 38f and 2- (t-butylamino) sulfonylphenyl boronic acid. 1 H NMR (400 MHz, CD 3 OD) d (ppm): 8.09 (dd, 1 H, J = 1.3 &7.9 Hz), 7.59 (dt, 1 H, J = 1.6 &7.6 Hz), 7.51 (dt , 1 H, J = 1.5 &7.8 Hz), 7.47 (bs, 1 H), 7.42-7.29 (m, 6H), 7.19 (dd, 1 H, J = 1.7 &8.3 Hz), 2.84-2.74 ( m, 2H), 2.05 (q, 1 H, J = 6.3 Hz), 1.72 (td, 1 H, J = 8.5 &5.7 Hz). Mass spectrum (LCMS, ESI pos.) Calculated for C23H19F3N3O2S: 458.1 (M + 1). Experimental 458.2.
BIOLOGICAL EXAMPLES EXAMPLE 1 Binding assay with human VR1 (hVR1) The compounds of the present invention were examined for the ability to inhibit [3H] RTX binding to hVR1 receptors in a [3H] RTX binding assay as previously described (Zhang, Sui-Po. Improved ligand binding assays for vanilloid receptors, PCT Int. Appl. (2002), WO 023341 1 A1 20020425 AN 2002: 315209, and Elfrida GR et al., J. Pharmacol. Exp. Ther., 2002, 300 (1): 9-17. ) HEK293 cells were transfected with the vanilloid hVR1 receptors and washed with Hank's balanced salt solution, dissociated with cell dissociation buffer (Sigma), and then centrifuged at 1000 xg for 5 min. The cell pellets were homogenized in cold 20 mM HEPES buffer (pH = 7.4), containing 5.8 mM NaCl, 320 mM sucrose, 2 mM MgCl 2, 0.75 CaCl 2 and 5 mM KCI and centrifuged at 1000 x g for 15 min. The resulting supernatant was then centrifuged at 40,000 x g for 15 min. The membranes converted to pellets were stored in a refrigerator at -80 ° C.
Approximately 120 pg of protein / ml of the membranes incubated with the indicated concentrations of [3H] RTX in 0.5 ml buffer HEPES (pH 7.4) containing 0.25 mg / ml of free bovine serum albumin Fatty acids at 37 ° C for 60 min. The reaction mixture was then cooled to 4 ° C, and 0.1 mg of glycoprotein a, -acid was added to each sample, which then incubated at 4 ° C for 15 min. The samples were centrifuged at 18, 500 x g for 15 min. The tip of the microcentrifuge tube was cut it contained the pellet. The bound radioactivity was quantified by scintillation counting.
The non-specific binding was measured in the presence of 200 nM unlabeled RTX.
The data was calculated according to the equation: % inhibition = 100% x [(total union-union) / (total union-union non-specific)] The values of K, were calculated by a Prism program.
TABLE 1 Comp. Ki (nM) Comp. Ki (nM) Comp. Ki (nM) 1 9.7 27 1800 71 22 3 20 32 100 78 6.4 4 31 36 820 79 18 5 17 40 81 310 10 9 0.9 50 16 312 19 14 380 51 6.4 319 6 15 41 56 120 407 5.7 17 8.7 69 6 434 39 18 6.5 70 8.6 EXAMPLE 2 Functional assay of human VR1 fhVRD The functional activity of the test compounds was determined by the measurement of changes in intracellular calcium concentration by a fluorescent dye sensitive to Ca ++ and FLIPR ™ technology. Increases in Ca ++ concentration were easily detected after stimulation with capsaicin. HEK293 cells expressing hVR1 were cultured in 384-well black-walled plates coated with poly-D-lysine (BD 354663) and 1 day later they were loaded with calcium dye 3 for 35 min at 37 ° C, 5% C02 and then for 25 min at room temperature and subsequently examined for agonist-induced increases in intracellular Ca2 + levels by FLIPR ™ technology. The cells were elicited with the test compounds (in varying concentrations) and the intracellular Ca2 + was measured for 5 min before the addition of capsaicin to all wells to achieve a final concentration of 0.030 μ? which produces approximately 80% of the maximum response. The IC50 values were determined from the concentration-response studies, which were generated using the average of the wells in quadruplicate for each point of the data. For the compounds tested, an IC50 value (nM) and the percentage inhibition value are shown in Table 2. Except where indicated, percentage inhibition values were obtained with a test concentration of 1 μ ?; otherwise: (1) the concentration of assay was 5 μ ?. The percentage inhibition value for the compounds when an IC50 value is not obtained. The term "ND" means that the data "is not available" because it was not obtained for a compound particular.
TABLE 2 Comp. % Inhib. ICso Comp. % Inhib. IC50 1 100 27 360 98 46 2 100 12 361 97 27 3 ND 140 362 99 8 4 78 400 363 98 12 5 100 71 364 97 65 6 12 ND 365 99 17 7 10 ND 366 99 35 8 10 ND 367 98 53 9 99 2 368 99 15 10 94 280 369 99 8 11 100 210 370 98 13 12 100 10 371 98 18 13 82 310 372 97 71 14 49 1000 373 99 20 15 100 120 374 99 34 16 100 45 375 97 139 17 100 8 376 100 28 18 100 4 378 100 12 19 32 ND 379 99 40 20 ND 320 380 99 12 22 ND 18 383 96 11 24 8 ND 384 98 7 25 4 ND 385 97 21 26 6 ND 386 96 43 27 100 260 387 98 41 28 96 250 388 99 54 29 6 ND 389 23 ND 30 10 ND 390 96 7 31 ND 13 391 95 8 Comp. % Inhib. IC50 Comp. % Inhib. IC50 32 77 380 392 97 10 33 ND 1700 393 98 10 34 (1) 75 ND 394 98 6 35 100 41 395 99 15 36 44 ND 396 99 13 37 18 ND 397 99 23 38 89 270 398 97 3 39 98 200 399 97 3 40 99 54 402 93 38 41 90 280 404 94 47 42 100 22 405 95 20 43 58 890 406 97 170 44 95 300 407 96 9 45 100 16 408 64 ND 46 100 46 409 43 ND 47 100 20 410 91 156 48 33 ND 411 85 350 49 16 ND 412 86 190 50 100 100 413 82 240 51 100 66 414 98 140 52 28 ND 415 95 150 53 98 47 416 96 120 4 20 ND 417 100 11 5 14 ND 418 100 18 6 100 1 10 419 93 32 7 15 ND 420 93 15 8 87 95 421 95 10 9 80 440 422 98 7 0 7 ND 423 99 1 1 1 100 75 424 99 1 1 2 100 200 425 2 ND 3 97 260 426 99 22 4 41 ND 427 98 13 5 0 ND 428 100 7 6 98 48 429 98 6 7 98 130 430 100 9 8 ND 329 431 97 35 9 98 6 432 98 15 0 100 7 433 98 10 1 99 22 434 98 7 7 100 76 435 97 20 8 99 5 436 96 10 9 100 7 437 97 24 3 ND > 500 438 96 71 4 100 40 439 97 23 Comp. % Inhib. IC50 Comp. % Inhib. IC50 85 16 ND 440 98 40 95 81 301 441 40 ND 101 ND > 500 442 96 4 113 48 ND 444 98 28 114 99 3 445 96 20 129 96 34 446 97 76 130 100 6 447 98 44 131 96 31 448 99 17 139 98 31 449 100 9 145 19 ND 450 27 ND 175 100 16 451 101 28 190 94 38 452 5 ND 198 95 10 453 22 ND 234 7 ND 454 36 ND 250 98 19 455 100 17 294 101 9.1 456 100 45 295 100 16 457 22 ND 309 73 ND 458 15 ND 310 100 6 459 0 ND 311 99 54 460 21 ND 312 100 6 461 99 5 314 100 18 462 98 97 315 100 1 1 463 100 14 316 101 12 464 100 3 317 101 1 1 465 75 363 318 100 50 466 98 71 319 100 10 467 86 182 320 100 13 468 97 8 321 100 18 469 99 7 322 101 14 470 97 45 323 97 40 471 100 10 324 98 33 472 ND > 500 325 73 ND 473 ND > 500 326 89 157 474 ND > 500 327 77 343 475 ND 77 328 99 35 476 ND 68 329 98 27 477 44 ND 330 85 131 478 ND > 500 331 97 43 479 12 ND 332 98 49 480 ND > 500 333 98 27 481 42 ND 334 94 178 482 100 13 335 100 47 483 21 ND 336 89 240 484 ND > 500 337 96 14 485 ND > 500 Comp. % Inhib. IC50 Comp. % Inhib. IC50 338 96 104 486 ND > 500 339 99 27 487 20 ND 340 98 62 488 4 ND 341 99 6 489 96 2 342 98 24 490 99 26 343 82 243 491 ND 77 344 101 24 492 99 5 345 101 13 494 93 52 346 87 264 497 94 39 347 100 44 498 100 19 348 86 162 499 7 ND 349 99 59 500 97 19 350 100 33 501 99 85 351 ND > 500 502 82 190 357 100 8 503 93 10 358 99 9 504 95 22 359 98 24 EXAMPLE 3 Inflammatory pain models induced in chemical form The compounds of the present invention were examined in animal models of inflammation and inflammatory pain. To evaluate the ability of the test compounds to reverse thermal hyperalgesia, the latencies of basal response in a paw stimulator were obtained by radiant heat (RH) before an intraplantar injection of 100 μ? (1 pg / μ?) CFA (1: 1 CFA: saline) in male Sprague-Dawley rats. Only registered withdrawal responses that were quick movements of the hind leg (with or without licking the rear leg). Paw movements associated with the Locomotion or weight change were not considered a withdrawal response.
The stimulus intensity that produced baseline withdrawal latencies of 10-15 seconds was used and a maximum limit of 20 seconds was imposed. It was evaluated hypersensitivity after CFA. Only the rats that showed so less a 25% reduction in response latency from the value basal (ie, hyperalgesia) were included for further analysis.
After evaluation of the post-flammable dormancy, the rats were dosed orally (2.5 ml / kg) with the test compound (10 mg / kg) or vehicle (hydroxypropyl beta cyclodextran 20%). To determine the time of the maximum effect, the latencies 30, 60 were again determined, 100, 180 and 300 min after the administration of the compound.
The data is presented as the reversion of the percentage of hypersensitivity obtained during the 300-min trial, which was calculated for each animal according to the formula: Reversion% = 100% x (response to treatment - response post-flammable) / (pre-flammable response - post-flammable response) TABLE 3 Comp. % Reversal 17 104 18 133 22 18 23 31 31 72 47 58 70 76 78 19 Comp. % Reversal 114 56 310 23 464 65 EXAMPLE 4 Post-operative surgery model induced by an incision The compounds of the present invention were examined in animal models of postoperative surgery, as previously described (Brennan, T.J. et al., Pain, 1996, 64: 493-501). Male rats were anesthetized Sprague-Dawley with 2-3% isoflurane and the plantar surface of the leg back was sterilized by three brushes alternating betadine and alcohol. HE made a longitudinal incision of 1 cm through the skin of the plantar foot using a number 10 scalpel that begins 0.5 cm from the proximal heel and It extends towards the toes. The plantaris muscle was excised through a clamp and a longitudinal incision was made. Then the skin was sutured in two places using 5-0 silk. The site of the wound was then covered with ointment antibiotic and the animals were returned to their individual cages. The changes of thermal sensitivity were evaluated before surgery and 24 hours after of surgery. Vehicle was administered orally (HPPCD 20%) or test compound and the thermal sensitivity was re-evaluated 30, 60, 100, 180 and 300 minutes later.
The data are presented as the percentage of maximum hypersensitivity reversion obtained during the 300-min test, which was calculated for each animal according to the formula:% reversion = 100% x (response to treatment - post-inflammatory response) / ( pre-inflammatory response - post-inflammatory response) TABLE 4 Comp. % Reversal 18 132 While the foregoing description teaches the principles of the present invention, with examples provided for the purpose of illustration, it will be understood that the practice of the invention encompasses all customary variations, adaptations and / or modifications that are within the scope of the invention. following claims and their equivalents. All publications described above in the specification are hereby incorporated by reference in their entirety.

Claims (17)

NOVELTY OF THE INVENTION CLAIMS
1. - A compound of formula (I):
(I) and a form thereof where: the dotted lines between positions 1, 2 and 3 of Formula (I) indicate the positions of a tautomeric double bond, where when a double bond is formed between positions 1 and 2, then R3b is present and where, when a double bond is formed between positions 2 and 3, then R3a is present; p is 1 or 2; q is 0 or 1; r is 0, 1, 2 or 3; L is alkyl d-3, C2-3 alkenyl, C2-3 alkynyl or cyclopropyl; A-i is selected from the group consisting of phenyl, biphenyl, naphthyl, pyridinyl, quinolinyl and indole; each Ri is selected from the group consisting of hydroxy, cyano, halogen, formyl, carboxy, alkyl, haloalkyl C-6, alkoxy Ci-6, haloalkoxy Ci-6, alkylcarbonyl C1-6, alkoxycarbonyl d-6, alkylthio d-6 , alkylsulfonyl d-6, cycloalkyl C3-8, cycloalkyl C3-8-alkyl C -4, cycloalkyl C3-8-alkoxy C1-4, cycloalkylC3-8-oxygen, amino, (alkyl d-6) i-2amino, ( C3-8 cycloalkyl) i-2-amino, (C3-8-alkyl d-) i-2arnino cyanoalkyl, aminocarbonyl, (Ci-6 alkyl) i-2 aminocarbonyl, Ci-6 alkylcarbonylamino, C6 alkoxycarbonylamino, aminocarbonylamino, (Ci. 6 alkylamino) aminocarbonylamino, Ci-6 alkylsulfonylamino, Ci_6 alkylsulfinylamino, aminosulfonyl, (Ci_4 alkyl) i-2 aminosulfonyl, aminosulfonylamino and (Ci_6 alkyl) i-2 aminosulfonylamino, where alkyl is optionally substituted with alkoxy d-β, amino, (C1-6 alkylcarbonylamino, alkoxycarbonylamino Ci-6) aminocarbonylamino, (Ci.6 alkyl) i-2 aminocarbonylamino, C1-6 alkylsulfonylamino, aminosulfonylamino, (Ci-alkyl) 6) i-2-arninosulfonylamino, hydroxy and phenyl, wherein the phenyl is optionally substituted with one, two or three substituents independently selected from the group consisting of halogen, cyano, nitro, Ci-6 alkyl, Ci.6 alkoxy, Ci-6 alkylthio and alkylsulfonyl-6 and wherein, each case of alkyl and alkoxy is optionally perfluorinated; R 2 is selected from the group consisting of halogen, C 1-4 alkyl, C 1-4 alkoxy, alkylsulfonyl d-4, nitro, amino, (C 1-4 alkyl) i-2 amino and cyano, wherein, each case of alkyl and alkoxy it is optionally perfluorinated; each R3a and R3b is selected from the group consisting of hydrogen and optionally perfluorinated Ci-4 alkyl; and each R 4 is selected from the group consisting of halogen, nitro, cyano, carboxy, alkyl d-6, alkoxy d-6, haloalkyl C-6, haloalkoxy Ci-6, alkoxy Ci-6-C 1-6 alkyl, alkylcarbonyl d -6, alkylthio d-6, haloalkylthio Ci-6, alkylsulfonyl d-6, haloalkylsulfonyl d-6, cycloalkyl C3-8, cycloalkyl C3.8-alkyl Ci-4, cycloalkyl C3-8-alkoxy Ci-4, cycloalkyl C3 -8-oxygen, amino, (Ci-6 alkyl) i-2 amino, (C3-8 cycloalkyl) i-2 amino, (C3-8 cycloalkyl-C3-8 alkyl) i.2 amino, aminocarbonyl, (alkyl) Ci-6) i-2 aminocarbonyl, alkylcarbonylamino d-6, alkoxycarbonylamino Ci-6, aminocarbonylamino, (C 1-6 alkyl) i-2 aminocarbonylamino, alkylsulfonylamino Ci-6, haloalkylsulfonylamino d-6. C 1-6 alkylsulfinylamino, aminosulfonyl and (Ci-4 alkyl) - | .2 aminosulfonyl, wherein each alkyl case is optionally substituted with one, two or three substituents independently selected from the group consisting of Ci-8 alkoxy, amino, (alkyl) 0-1.4) 1-2 amino, alkylcarbonylamino d.6, alkoxycarbonylamino d-6, aminocarbonylamino, (C6 alkyl) i-2 aminocarbonylamino, alkylsulfonylamino Ci_6, oxo and hydroxy, and where, each case of alkyl and alkoxy is optionally perfluorinated . 2 - The compound according to claim 1, further characterized in that q is 0.
3. The compound according to claim 1, further characterized in that Ai is selected from the group consisting of phenyl, biphenyl, naphthyl, quinolinyl and indole. .
4. The compound according to claim, further characterized in that each Ri is selected from the group consisting of hydroxy, halogen, formyl, C1.6 alkyl, Ci-6 haloalkyl, haloalkoxy d.6, alkylcarbonyl d.6 alkoxycarbonyl d 6, alkylthio -6, alkylsulfonyl d.6, amino, aminocarbonyl, alkylcarbonylamino d-6, alkoxycarbonylamino d.6, alkylsulfonylamino d-6, aminosulfonyl, (Ci-4 alkyl) i-2 aminosulfonyl and aminosulfonylamino, where alkyl is optionally substituted with amino, (C 1-4 alkyl) i-2 amino, aminosulfonylamino or hydroxy, and wherein the alkyl is optionally perfluorinated.
5. The compound according to claim 1, further characterized in that R 2 is selected from the group consisting of halogen and C 1 alkyl, wherein the alkyl is optionally perfluorinated.
6. The compound according to claim 1, further characterized in that each R3a and R3b are selected from the group consisting of hydrogen and C- alkyl.
7. The compound according to claim 1, further characterized in that each R4 is selected from the group consisting of halogen, carboxy, alkyl d-6, alkoxy Ci-6, haloalkyl Ci-6, haloalkoxy C-6, alkylcarbonyl Ci -6, haloalkylthio d-6, alkylsulfonyl d-6, haloalkylsulfonyl C1-6, (C1-6 alkyl) i-2 amino, (Ci-6 alkyl) i-2 aminocarbonyl, alkylcarbonylamino Ci_6, alkylsulfonylamino d-6 and haloalkylsulfonylamino Ci -6, wherein alkyl and alkoxy are optionally perfluorinated.
8. The compound according to claim 1, further characterized in that p is 1 or 2; q is 0; r is 0, 1, 2 or 3; L is alkyl Ci.3, C2-3 alkenyl, C2-3 alkynyl or cyclopropyl; is selected from the group consisting of phenyl, biphenyl, naphthyl, quinolinyl and indole; each R1 is selected from the group consisting of hydroxy, halogen, formyl, alkyl d-6, haloalkyl C-1.6, haloalkoxy Ci-6, alkylcarbonyl C1-6, alkoxycarbonyl Ci-6, alkylthio Ci-6, alkylsulfonyl Ci-6, amino, aminocarbonyl, alkylcarbonylamino d-6, alkoxycarbonylamino d-6, alkylsulfonylamino d-6, aminosulfonyl, (Ci-4 alkyl) i-2 aminosulfonyl and aminosulfonylamino, where the alkyl is optionally substituted by amino, (alkyl d-4) - .2 amino, aminosulfonylamino or hydroxy, and wherein, the alkyl is optionally perfluorinated; R2 is selected from the group which consists of halogen and C- alkyl, where alkyl is optionally perfluorinated; each R3a and R3b is selected from the group consisting of hydrogen and C- alkyl; and each R4 is selected from the group consisting of halogen, carboxy, C-6 alkyl, Ci-6 alkoxy, Ci-6 haloalkyl, Ci-6 haloalkoxy, alkylcarbonyl C-i.6, haloalkylthio C -6 > Ci-6 alkylsulfonyl, Ci-6 haloalkylsulfonyl, (C1-6 alkyl) 1-2 amino, (Ci-6 alkyl) i-2 aminocarbonyl, alkylcarbonylamino C-i-6, alkylsulfonylamino Ci-6 and haloalkylsulfonylamino Ci-6, where alkyl and alkoxy they are optionally perfluorinated.
9. A compound selected from the group consisting of: (E) -1- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, (E) -1- (2- { 2- [2- (4-tert-butyl-phenyl) (E) -2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] - 1 H-benzimidazol-5-yl.} - phenol, (£) -N- (2- {2 - [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazole-5 -yl.}.-phenyl) -amide, (£) -2-. {2- 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. benzamide, (E) -3- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -benzamide, (E) -4 - { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -benzamide, (E) -N- (4-. {2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -amide, (E) -N- (2-. {2- 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanesulfonamide, tert-butyl ester of (£) - (2-. {2- 2- - (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -carbamic acid, (£) -2- { 2- [2- (4-ter- butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenylamine, (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H-benci midazol-5-il} phenyl) -methanol, (E) -2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (E) -1- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -ethanone, (£) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, (E) -N- (2 - { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -2- (2-. {2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, (E) -2-. { 2- [2- (4-Trifluoromethoxy-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzamide, (£) -1- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-ylH-ethanone, (E) -1- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl) -1 H -benzimidazol-5-yl} phenyl) -ethanol, 5 (E) -N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) - methanesulfonamide, (E) -2- (2- { 2- [2- (4-tnfluoromethoxy-phenyl) -vinyl) -1 H -benzimidazol-5-yl} phenyl) -propan-2-ol, (£) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} .-phenyl) -acetamide, (£) -N- (3- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl ) - acetamide, (£) -2-. { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzamide, (E) -1- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, Q (E) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- . { 2- [3- (4-tert-Butyl-phenyl) -propyl) -1H-benzimidazol-5-yl} -phenol, 2- [3- (4-tert-butyl-phenyl) -propyl] -5-m-tolyl-1 H-benzimidazole, N- (2- { 2- [2- (4-trifluoromethyl- phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 3-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 4-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, (E) - (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenmethanol, (E) -2- {.2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (E) -N- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, (E) -2 -. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, (E) -1- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, (E) ) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 0 (E) -2- . { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (£) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl'-methanol, (E ) -N- (2- {2- [2- (4-tnfluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} - phenyl) -acetamide, (£) -2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, (£) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl] -ethanol, 1- (2- { 2- [2- (4-Trifluoromethanesulfonyl-pheny] -etl] -1 H -benzimidazol-5-yl.} - phenyl] -ethanol, ( £) -2- (2- { 2- [2- (4-tnfluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, (E )-2-. { 2- [2- (4-tert-butyl-phenyl] -v] nyl] -6-trifluoromethyl-1H-benzimidazole-5-yl} -phenol, (E) -3-. { 2- [2- (4-tert-Butyl-pheny] -vinyl] -6-trifluoromethyl-1H-benzimidazol-5-yl} -phenol, (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzimidazole- 5-yl.}.-Phenyl) -acetamide, (E) - (2- { 2- [2- (4-tert-butyl-phenyl) -v-n-1] -6-tr Fluorometyl-1 H-benzimidazol-5-yl.} - phenyl) -methanol, (£) -2- [2- (4-tert-butyl-phenyl) -v-n-1 ] -5- (2-fluoro-phenyl) -6-trifluoromethyl-1H-benzimidazole, (£) -2-. { 2- [2- (4-tert-Butyl-pheny] -vinyl] -6-trifluoromethyl-1H-benzimidazo-U-benzamide, tert-butyl ester of the acid (£) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl}. -phenyl) -carbamic acid, (E) -N- (2- {. 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimid phenyl) -methanesulfonamide, (E) -N- (2-. {6-trifluoromethyl- 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, (E) -1- (2-. {6-trifluoromethyl-2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzyl-5-yl.} - phenyl) -ethanone, (E) - (2-. {6-trifluoromethyl-2- [2 - (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -fen (E) -3-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-i E) - (2-. {6-fluoro-2- [2- (4- trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanol, (E) -1- (2-. {6-fluoro-2- [2- (4-trifluoromethyl- phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, (E) -2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide, (£) -N- (2- {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) - acetamide, (E) -N- (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide , (E) - (2-. {6-Chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) ) -1- (2- {6-doro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole ^ phenyl) -ethanone, (£) -2-. { 6-chloro-2- [2- (4-trifluoromethyl-phenyl) -vin] -1-H-benzimidazol-5-yl} -phenol, (E) -2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzyldazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (- =) - 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -v] nyl] -1H-benzimidazole -5-yl.}.-Phenyl) -methanesulfonamide, (£) -C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -C, C, C-trifluoro-N- (2-. {2- 2- (4 -trifluoromethanesulfonyl-phenol) -v] nyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (£) -1- (2-. {2- 2- [2 - (4-chloro-phenyl) -vinyl] -1 H-benzimidazol-5-yl.] - phenyl) -ethanone, (E) -1- (2-. {2- 2- [2 - (4-chloro-phenyl) -vi ^^ (£) -N- (2- { 2- [2- (4-chloro-phenyl) -vin] -1-H-benzimidazole-5 -l.}.-Phenyl) -methanesulfonamide, (E) -2- (2- { 2- [2- (4-chloro-pheny] -vinyl] -1 H -benzyldazole -5-.l.].-Phenyl] -propan-2-ol, (£) -2- { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzyl midazol-5-yl.} - benzenesulfonamide, (E) -N- (2- { 2- [2- (4-chloro-pheny] -v] nyl] -1 H-benzyl midazol-5-tl.}.-phenyl) -C >; C, C-trifluoro-methanesulfonamide, (£) -1- (2-. {2- 2- [4- (methanesulfonyl-phenyl) -vinyl] -1H-benzimidazole-5- L.}.-Phenyl) -ethanone, (E) -1- (2-. {2- 2- [2- (4-methanesulfonyl-pheny] -v] n-1] -1 H-benz midazol-5-yl.}.-phenyl] -ethanol, (£) -N- (2- {2- [2- (4-methanesulfonyl-phenyl) -v] nyl] -1 H-benzimidazole -5-yl.}.-Pheny] -metanesulfonamide, (£) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -v] nyl] -1 H -benzim dazol-5-yl.}. phenyl) -propan-2-ol, (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -C, C, C-trifluoro-N- (2- { 2- [2- (4-methanesulfonyl-phenol) -v, nl] -1 H- benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (?) - 1- [2- (2- { 2- [4- (2,2,2-? p ???? G? -1-1p ???? G? Gt ?? 1? ?? - T ????) - ?????] - ??? · | ?.}. -1? -benzimidazole -5-yl) -phenyl] -ethanone, (£) -1- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy ) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -ethanol, (E) -N- [2- (2-. {2- 2- [2 ( 2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -v, n-1., -1 H-benzyldazol-5-yl) -phenyl] -methanesulfonamide , (E) -2- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phen] -v 1.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, (£) -2- (2- { 2- [4- (2,2,2- trifluoro-1-tr¡fluoromet¡l-etox¡) -fen¡l] -v¡nil.}. -1 H-benzimidazol-5-¡l) -bencensulfonam¡da, (E) -C, C, C -trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl] -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide, (£) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] - v inyl.) -1 H-benzimidazoi-5-yl) -phenyl] -ethanone, (E) -1- [2- (2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl} -1H-benzamdazol-5-yl) -phenyl] -ethanol, (£) -N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro) -ethoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -2- [2- (2-. {2- 2- [ 4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl] -1H-benzimidazol-5-yl) -phenyl] -propan-2-ol, (E) -2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -v-nyl} -1-H-benzimidazol-5-yl) -benzenesulfonamide, (/ 5) -C, C) C-tnfluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl ] -vinyl. -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- [2- (2-. {2- 2- (2,2,3 , 3,3-pentafluoro-propoxy) -phenyl] -v-n-1] -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (E) -1- [2- ( 2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -v-nil.} -1 H-benzimidazol-5-yl. ) -pheny] -ethanol, (£) -N- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -metanesulfonamide, (E) -2- [2- (2- { 2- [4- (2,2,3,3,3 -pentafluoro-propoxy!) -phenyl] -vinyl. -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, (E) -2- (2-. {2 - [4- (2,2,3,3,3-pentafluoro-propoxy) -fenN] -vinyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2,213> 3.3 -pentafluoro-propox¡) -phenyl] -v¡n¡l.}. -1 H-benc¡midazol-5-¡l) -phenyl] -methanesulfonamide, (E) -1- (2- { 2 - [2- (3-chloro-phenyl) -vinyl] -1H-benzamidazol-5-yl] -phenyl) -ethanone, (E) -1- (2-. {2- 2- [2 - (3-Chloro-phenyl) -v-n-1] -1 H -benzimidazol-5-yl.} - -pheni (£) -N- (2-. {2- 2- (3-chloro phenyl) -v, nl] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (£) -2- (2- { 2- [2- (3- chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl.] -phenyl] -propan-2-ol, (E) -2-. {2- 2- [ (3-chloro-phenyl) -vinyl] -1H-benzimidazole-5-yl.] -benzenesulfonamide, (E) -N- (2-. {2- 2- (3- (3- chloro-phenyl) -vinyl] -1 H-benzimidazol-5-yl.] - phenyl] -C, C, C-trifluoro-methanesulfonamide, (E) -1- (2- {. 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, (£) -1- (2-. {2- 2- ( 3-trifluoromethyl-phenyl) -vinyl] -1 H-benzimidazol-5-yl.}. -phenyl) -ethanol, (£) -N- (2- { 2- [2- (3-tr¡fluorometil phenyl) -villin] -1 H-ben cimidazol-5-yl.} - phenyl] -metanesulfonamide, (E) -2- (2-. { 2- [2- (3-trifluoromethyl-phenyl] -vin] -1-H-benzyldazol-5-yl} phenyl) -propan-2-ol, (E) -2-. { 2- [2- (3-trifluoromethyl] -phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (F) -C, C, C-trifluoro-N- (2. {2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzyl midazol-5-yl.} - phenyl] -methanesulfonamide, (E) -N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -vnil.}.-phenyl] -methanesulfonamide, (E) -N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -pheny] - 1 H-benc¡m¡dazol-2-¡l} -v¡nil) -phenyl] -.. methanesulfonamide, (E) -N- (2- {2- [2- (4-metansulfon¡lamino.. phenyl) -vinyl] -1H-benzyldazole-5-yl.} - phenol) -methanesulfonamide, (£) -N- [4- (2- { 5- [2 - (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - vinylamino) - ^ phenyl] -methanesulfonamide, (E) -2-. { 2- [2- (4-methanesulfonylamine-phenol) -vinyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl} -1 H- benzyl) midazol-5-yl.}. phenyl) -methanesulfonamide, (E) -N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1 H -benzyldazole-2- L] -vinyl-N-C, C, C-trifluoro-methanesulfonamide, (E) -C, C, C-trifluoro-N- [4- (2-. {5- [2] - (1-Hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl.] - vinyl) -phenyl] -methanesulfonamide, (E) -C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H -j-benzamidazol-2-yl] -v-nil}. phenyl) -metanesulfonamide, (£) -C, C, C-tnfluoro-N- [4- (2- { 5- [2- (1-hydroxy-1-methylene-ethylene) -phenyl] -1 H- benzimidazol-2-yl.] - vinyl) -phenyl] -methanesulfonamide, (E) -2-. { 2- [2- (4-trifluoromethanesulfonylamine-phenyl) -v] nl] -1 H-benzimidazol-5-yl} - Benzenesulfonamide, (E) -C, C, C-trifluoro-N- (4-. {2- 2- [2- (2-trifluoromethanesulfonyllamine-phenol) -1 H- benzyl Midazol-2-yl] -vinylamino] -phenyl) -methanesulfonamide, 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -15 benzenesulfonamide, 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2-. {2- [2- (4-trifluoromethoxy-phenol) -etl] -1H-benzimidazole-5 - il.}. - pheny!) - methanesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazole-5} -yl.}. - phen.l) -methanesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-pheny] -ethyl] -1 H- benzamidazol-5-yl.] - phenyl] -methanesulfonamide, 1- (2- {2- [2- (4-chloro-phenyl) -ethyl] -H-benzimidazole-5-) il.}. phenyl) -ethanone, 20 1 - (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) - ethanol, N- (2- {2- [2- (4-chloro-phenyl) -ethyl] -1 H -benzyldazol-5-yl} -phenyl) -methanesulfonamide, 2- ( 2- {2- [2- (4-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -propan-2-ol, 2-. { 2- [2- (4-chloro-phenyl) -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, N- (2-. {2- 2- [2- (4-chloro-pheny] -ethyl] -1 H -benzimidazole-5-yl.} -phenl) -C, C , C-trifluoromethanesulfonamide, 1- (2- {2- [2- (4-methanesulfonyl-phenyl) -ethyl] -H-benzimidazol-5-yl} -phenyl) -ethanone, - (2- { 2- [2- (4-Methanesulfonyl-pheny] -ethyl] -1 H -benzyldazol-5-yl.} - phenyl) -ethanol, N- (2 - { 2- [2- (4-Methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (4-methanesulfonyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, C >; C, C-trifluoro-N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimide phenyl) -methanesulfonamide, 1 - [2- ( 2- {2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl} -etyl} -1 H-benzimidazol-5-yl) - phenol] -ethanone, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2- { 2- [4- (2,2,2-tnfluoro-1-tnfluoromethyl-ethoxy ) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-tr! fluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. {2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzyldazol-5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -eti l.}. -1 H-benzimidazol-5-yl) -phenyl] -metanesulfonamide, 1 - [2- (2-. {2- 2- [4- (2,2,2-trifluoro- ethoxy!) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2-. {2- 2- [2- (2,2- 2-trifluoro -ethoxy) -phenyl] -etyl] -1 H-benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -etl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl) ] -etl.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. {2- 2- [4- (2,2,2-trifluoro- ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, C, C, C-trif luoro-N- [2- (2-. {2- 2- [ 4- (2, 2, 2-trifluoro-ethoxy) -phenyl] -ethyl.} - 1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- [2- (2- {.2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanone 1- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzyl dazol-5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- [4- (2,2,3,3l3-pentafluoro-propoxy) -phenyl] -ethyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) - phenol] -ethyl.} -1 H-benzyldazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. {2- 2- [2- (2,2,3 , 3,3-pentafluoro-propoxy) -phenyl] -etyl] -1 H-benzyldazol-5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [ 2- (2- { 2- [4- (2,2,3,3,3-p entafluoro-propoxy) -phenyl] -etl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- (2- { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazole-5-yl; l.}. -phenyl) -ethanone, 1 - (2- { 2- [2- (3-chloro-pheny] -ethyl] -1 ^ N- (2- { 2- [2 - (3-chloro-phenyl) -etl] -1 H -benzimidazol-5-yl.} - phenyl] -methanesulfonamide, 2- (2-. {2- 2- (3-chloro phenyl) -ethyl] -1 H -benzyldazol-5-yl.} - phenyl) -propan-2-ol, 2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H-benzyldazole-5-yl.] - benzenesulfonamide, N - (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzim Dazol-5-yl.}.-Phenyl) -C, C, C-trifluoro-methanesulfonamide, 1- (2-. {2- 2- [2- (3-trifluoromethyl-phenyl) -eti] -1H-benzimidazol-5-yl.} - phenyl] -ethanone, 1- (2- { 2- [2- (3-Trifluoromethyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl.} -phenl) ^^^ N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -etl] -1 H -benzyldazole-5-yl.} - phenyl] - methanesulfonamide, 2- (2- { 2- [2- (3-trifluoromethyl-phenol) -etl] -1 H-benzimidazole-5-yl.} -phenol ) -propan-2-ol, 2-. { 2- [2- (3-trifluoromethyl-phenyl] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl} -1 H -benzimidazol-5-yl} -phenol ) -metanesulfonamide, N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -ethyl} -phenyl) -methanesulfonamide, N- [4- (2- { 5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazol-2-yl.] -etl] -phenyl] -methanesulfonamide, N - (2- { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzylnidazol-5-yl.] - phenyl) -methanesulfonamide, N- [ 4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzyldazole-2-yl} -ethyl ) -phenyl] -methanesulfonamide, 2-. { 2- [2- (4-methanesulfonyllamino-pheny] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2-. {2- [2- (4-methanesulfonylamino-pheny] -ethyl] -1 H -benzyldazol-5-yl}-phenyl) -metanesulfonamide, N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzyldazol-2-yl] -etyl}. -phenyl) -C, C, C-trifluoro-methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) ) -phenyl] -1H-benzimidazol-2-yl.] -ethyl) -phenyl] -methanesulfonamide, C, C, C-trifluoro-N- (4-. {2- 2- [5- ( 2-methanesulfonyllamine-phenyl) -1 H -benzyldazol-2-yl] -ethyl] -phenyl) -methanesulfonamide, C, C, C-trifluoro-N- [4- (2- { 5- [2- (1- ^ 2 -l.}. -etll) -fenl] -metanesulfonamide, 2- { 2- [2- (4-trifluoromethanesulfonilamno-phenyl ) -etl] -1 H-benzyldazol-5-yl.] - benzenesulfonamide, C, C, C-trifluoro-N- (2-. {2- 2- (4-tr Fluoromethanesulfonyllamino-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. {2- 2- [2- (4-trifluoromethoxy-phenyl) - Cyclopropyl] -1H-benzyldazole-5-yl.] - benzenesulfonamide, 2-. {2- 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyl midazole-5-.l. -benzenesulfonamide, 2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethoxy-pheny] -cyclopropyl] -1H-benzimidazol-5-yl .}.-phenyl) -methanesulfonamide, C, C, C-tnfluoro-N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazole-5- il.}.-phenyl) -methanesulfonamide, C, C, C-trifluoro-N- (2-. {2- 2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazole -5-yl.}.-Phenyl) -methanesulfonamide, 1- (2- {2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -fen L) -etanone, 1- (2- { 2- [2- (4-Chloro-phenyl) -cyclopropyl] -1 H -benzyldazol-5-yl.} - phenyl) -ethanol, N - (2- { 2- [2- (4-chloro-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. 2- [2- (4-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, N ^^ - ^^ - chloro-phene-cyclopropyl-I H-benzimidazol-S-ilHeni -CCC-trifluoro-methanesulfonamide, 1- (2- { 2- [2- (4-methanesulfonyl-phen L) -cyclopropyl] -1 H-benzimidazol-5-yl.] - phenyl] -ethanone, 1- (2- {2- (2- (4-methanesulfonyl-phen L) -cyclopropyl] -1H-benzyldazole-5-yl] -phenyl] -ethanol, N- (2-. {2- [2- (4-methanesulfonyl) -pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- [2- (4-methanesulfonyl-phenyl) ) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl) -1 H -benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl}. phenyl) -metanesulfonamide, 1- [2- (2 { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) ) -phenyl] -cyclopropyl] -1 H-benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- 4- (2,2, 2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2-. {2- 2- [4- (2,2,2-tnfluoro-1-tnfluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl] -1 H-benzimidazol-5-yl) -benzenesulfonamide, C , C, C-tnfluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1 H- benzimidazol-5-yl) -phenyl] -methanesulfonamide1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] - ethanone, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazole- 5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl.] -1 H-benzimidazole -5-yl) -phenyl] -methanesulfonamide, 2- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl.] -1 H- benzimidazol-5-yl) -5-phenyl] -propan-2-ol, 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl}. 1H-benzimidazol-5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2,2,2-tnfluoro-ethoxy) -phenyl] - cyclopropyl.} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- [2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propoxy ) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2-. {2- 2- [2- (2,2,3,3, 3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- 4- (2,2 , 3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.} -1 Ho ben cimidazol-5-yl) -phenyl] -metanesulfonamide, 2- [2- (2-. { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, C, C >C-trifluoro-N- [2- (2-. {2- 2- [4- (2I2,3,3) 3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- (2- { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} .-phenyl) -ethanone, 1- (2- {2- [2- (3-chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -ethanol, N- (2-. {2- [2- (3-chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -5-methanesulfonamide, 2- (2-. {2- [2- (3-chloro-phenyl) ) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, N- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl) -1 H -benzimidazol-5-yl} phenyl) -C, C, C-trifluoro-methanesulfonamide, 1- (2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - phenyl) -ethanone, 1- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -0 ethanol, N- ( 2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, 2- (2-. {2- 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - Benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzamidazole- 5-yl.}.-Phenyl) -metanesulfonamide, N- (4-. {2- 2- [2- (2-acetyl-phenol) -1 H -benzyldazole-2-yl] - cyclopropyl] -phenyl) -methanesulfonamide, N- [4- (2-. {5- [2- (1-Hydroxy-ethyl) -phenyl] -1H-benzimidazole- 2-alkyl) -cyclopropyl) -phenyl] -methanesulfonamide, N- (2- { 2- [2- (4-methanesulfonyllamine-phenol) -cyclopropyl] -1H -benzimidazol-5-yl.} - 5-phenyl) -methanesulfonamide, N- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl] -phenyl] -1H-benzimidazole-2-yl.] -cyclopropyl) -phenyl] -methanesulfonamide, 2-. { 2- [2- (4-methanesulfonyllamine-phenol) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl ) -metanesulfonamide, N- (4-. {2- 2- [5- (2-acetyl-phenyl) -1H-benzimidazol-2-yl] -cyclopropyl} -phenol) -C, C, C- trifluoro-methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1H -benzyldazole-2-yl.) -|j-cyclopropyl) -phenyl] -metanesulfonamide, C, C, C-tNfluoro-N- (4-. {2- 2- [5- ( 2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl.} - phenyl) -methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2 - (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzyl 2-yl.] -cyclopropyl) -phenyl] -methanesulfonamide, 2-. { 2- [2- (4-trifluoromethalisulfonyl) ilyl] -benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) - cyclopropyl] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- [2- (4-trifluoromethoxy-phenylethynyl) -1 H -benzimidazol-5-yl] -1,5-benzenesulfonamide, 2- [ 2- (4-trifluoromethyl-phenletin) -1 H-benzimidazol-5-yl] -benzenesulfonamide, 2- [2- (4-trifluoromethanesulfonyl-phenylethyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-Trifluoromethoxy-phenletin) -1 H-benzamdazol-5-yl] -phenyl-methanesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl-methanesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenletin) -1 H-benzimidazol-5-yl] -phenyl} -metansulfonamida, 20 1-. { 2- [2- (4-Chloro-phenyletyl] -1 H-benzyldazol-5-yl] -phenyl} -etanona, 1-. { 2- [2- (4-chloro-phenylethyl) -1 H-benzyldazol-5-yl] -phenyl} -etanoll N-. { 2- [2- (4-chloro-phenylethenyl) -1H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 2- . { 2- [2- (4-Chloro-phenylethenyl) -1 H-benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (4-chloro-phenylethenyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-trifluoromethanesulfonamide, 1-. { 2- [2- (4-methanesulfonyl-phenylethyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 1-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-tl] -phenyl} -etanol, N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} - methanesulfonamide, 2-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl-methanesulfonamide, 5- 1 - (2-. {2- 2- [4- (2,2,2-tnfluoro- 1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 1 - (2-. {2- 2- [4- (2,2,2-trifluoro-1 -tnfluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, N- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2 -ol, 2-. { 2- [4- (2,2,2-Tnfluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 1 0 C, C, C-tnfluoro-N- (2- { 2- [4- (2,2,2-tnfluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1H-benzimidazole- 5-yl.}.-Phenyl) -metanesulfonamide, 1- (2 { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} .-phenyl) -ethanone, 1 - (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) - ethanol, N- (2- {2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, 2- ( 2- {2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} -phenyl) -propan-2-ol,? 5 2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [4- (2,2,2-trifluoro-ethoxy) -phenylethynyl] -1 H -benzimidazol-5-yl}. phenyl) -metanesulfonamide, 1- (2 { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 1- (2- { 2- [4- (2, 2,3,3, 3-pentafluoro-propoxy!) -phenethyl] -1H-benzamidazole-5 -l.} - phenyl) -ethanol, N- (2- {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethynyl] -1H-benzimidazole-5 -yl.}. - phenyl) -methanesulfonamide, 2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethynyl] -1H-benzimidazole-5 -yl.}. - phenyl) -propan-2-ol, 2-. { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethynyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [4- (2,2,3 >3,3-pentafluoro-propoxy) -phenylethynyl] -1H-benzimidazol-5-yl} phenyl) -metanesulfonamide, 1-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 2-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, N-. { 2- [2- (3-Chloro-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} -metansulfonamide, 1- . { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} Ethanol, 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, N-. { 2- [2- (3-Chloro-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} -C, C, C-trifluoro-methanesulfonamide, 1 -. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanone, 1- . { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanol, N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (3-trifluoromethyl-phenylethynyl) -1H-benzimidazol-5-yl] -benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl-methanesulfonamide, N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -metanesulfonamide, N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl}. Phenyl) -methanesulfonamide, N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl) -phenyl} -metanesulfonamide, N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl} -phenyl) -methanesulfonamide, 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metansulfonamide, N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethynyl] -phenyl} -C, C, C-tnfluoro-methanesulfonamide, C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazole-2- il-ethynyl.}. phenyl) -methanesulfonamide, C, C, C-trifluoro-N-. { 4- [5- (2-methanesulfonylamino-phenyl) -1H-benzimidazol-2-yl-ethynyl] -phenyl} methanesulfonamide, C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl-ethynyl}-phenyl) -metanesulfonamide, 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, C, C, C-tnfluoro-N-. { 2- [2- (4-trifluoromethanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, (£) -N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-hydroxy-1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) - ethanone, (E) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -v-n-1] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (3-bromo-4-fluoro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-dimethylamine-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-fluoro-4-tnfluoromethyl-phenyl) -vinyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2-fluoro-4-trifluoromethy1-phenyl] -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-chloro-4-fluoro-phenyl] -v] nyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-fluoro-5-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (2,3,4-trifluoro-phenyl) -v! N!!] - 1 H-benzimidazol-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (2,4,5-trifluoro-phenyl) -v] n-1] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2,3-difluoro-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (2,5-difluoro-pheny] -vinyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,6-difluoro-phenyl] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (3,5-d-fluoro-phenyl] -vin] -1-H-benzyldazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3,4-d.fluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-Fluoro-2-trifluoromethy1-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl] -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (^^^ - ^ - (S ^ -bis-trifluoromethyl-phene-vinyl-I H-benzimidazol-S-yl-N-methyl-benzenesulfonamide, (£) -2- { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (E) -2-. {2- [2- 2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (Z5) -2-. {2- 2- [2- ( 2-chloro-6-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (£) -2- { 2- [2- (2,4-dichloro -phenyl) -vinyl] -1H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (£) -2- { 2- [2- (3-bromo-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (E) -2- { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (£) -2-. {2- 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - N-methyl-benzenesulfonamide, (£) -N-methyl-2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl ) -v -nl] -1 H-benzyldazol-5-yl.} - benzenesulfonamide, (E) -N-methyl-2- { 2- [2- ( 4- trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (2-trifluoromethyl-phenol) -v-n-1] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzyldazole-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (4-trifluoromethoxy-pheny] -v-n-1] -1 H -benzyldazole-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-Chloro-phenyl) -v-n-1] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (2-bromo-phenyl] -v] nyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-difluoro-phenyl] -v] nyl] -1 H -benzyldazol-5-yl} -N-methyl-benzenesulfonamide, N-methyl-2-. { 2- [2- (3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3,4-difluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,3-difluoro-phenyl] -v] nyl] -1 H -benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,5-difluoro-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (3,5-difluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-bromo-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamida, (E) -2-. { 2- [2- (2-trifluoromethyl-phenyl) -v-n-1] -1H-benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -H-benzimidazol-5-yl} -benzenesulfonamide, (-2- { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, (E) -2-. 2- [2- (4-fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, (E) -2-. {2- [2- (2 -fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - benzenesulfonamide, (£) -2- { 2- [2- (4-fluoro-3-trifluoromethyl- phenyl) -vinyl] -1H-benzimidazol-5-yl.} - c-benzenesulfonamide, (E) -2- { 2- [2- (2,3,4-tnfluoro-phenyl) -vinyl] - 1 H-benzimidazol-5-yl.} - benzenesulfonamide, (E) -2-. {2- 2- [2- (2,4,5-trifluoro-phenyl) -vinyl] -1H-benzimidazole-5 il.) - benzenesulfonamide, (£) -2-. {2- 2- [2- (2,6-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, (E ) -2- { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, (£) -2- { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - JQ benzenesulfonamide, (E) -2-. {2- 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] - H-benzimidazol-5-yl.} - ben censulfonamide, (E) -2-. { 2- [2- (3-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, (E) -2-. { 2- [2- (4-trifluoromethylsulfan'yl-phenyl) -vinyl] -1H-benzimddazol-5-yl} - benzenesulfonamide, 2- 2-. { 2- [2- (4-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (2,3,4-trifluoro-phenyl) -ethyl) -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,4,5-trifluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,6-difluoro-phenN) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (2,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -etiI] -1 H -benzimidazol-5-yl} -20 benzenesulfonamide, 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (2,4-difluoro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3,4-difluoro-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,3-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,5-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3,5-d.fluoro-phenyl) -etl] -1 H -benzyldazole-5-yl} -benzenesulfonamide, 2- (2-phenethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2-Chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Fluoro-2-tnfluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -N- (2- {2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) ) -N- (2- {2- [2- (4-isopropyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (£) -N- ( 2- {2- [2- (3-chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) -N- (2 - { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (£) -N- (2- {2- [2- (4-difluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- (2-. {2- 2- [ 2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N-. { 2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, (E) -N- (2- {2- [2- (4-dimethylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (£ ) -N- (2- {2- [2- (4-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (£) -N-. { 2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl >; -metanesulfonamide, (E) -N- (2- { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide , (E) -N- (2- { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- (2- { 2- [2- (2-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, -. { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Fluoro-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, (E) -2-. { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl] -vinyl] -1H-benzyldazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-ethoxy-phenol) -v-n-1] -1 H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2- (2-etyryl-1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-isopropyl-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl) -benzenesulfonamide, (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -v-n-1] -1 H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -v-n-1] -1 H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-phenyl) -vin] -1 H-benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-difluoromethyl-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,4-dichloro-phenyl] -v] nyl] -1 H -benzyldazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -v] nl] -1 H-benzyldazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-ethoxy-phenyl] -vinyl] -1 H -benzyldazol-5-yl} -benzenesulfonamide, (E) -4-fluoro-2-. { 2- [2- (4-Trifluoromethyl-phenyl) -vin] -1-H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -N- (2-. {3-methyl-2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -3H-benzamidazole-5-yl. .phenyl) -metanesulfonamide, (E) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, 4- trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1H-benzyldazole-5-yl} -benzenesulfonamide, 5- trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl] -ethyl] -1 H -benzyldazol-5-yl} -benzenesulfonamide, (E) -1- [4- (2- { 5- [2- (1-Hydroxy-1-methyl-etl) -phenyl] -1 H -benzimidazole -2-yl.}.-Vinyl) -phenyl] -ethanone, (E) -2-. { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, (£) -N-isopropyl-4-. { 2- [5- (2-methylsulfamoyl-phenyl) -H-benzimidazol-2-yl] -vinyl} - benzamide, (E) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -N- (4-. {2- 2- [2- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) - acetamide, 5 Acid (E) -4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} - benzoic, (E) -2-. { 2- [2- (1 H-indol-6-yl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, N- (2- {2 - [2- (4-tnfluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) -acetamide, 1 (E) -2.2,2-tnfluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -acetamide , (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (E) -2.2.2 -trifluoro-ethanesulfonic acid, (iE) -2,2-dimethyl-N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidaz phenyl) -propionamide, (2-. {(2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -am of (E) -ethanesulfonic acid, Methyl ester of (E) - acid (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -carbamic acid; 5 (E) -2- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2- ol, 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -feni Ethyl ester of (E) -2- acid. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzoic acid, N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -2- [2- (2-styryl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 20 (Z) -2- (2- { 2- [2- (4-trifluoromethyl- phenyl) -vinyl] -1H-benzimidazol-5-ylH ^ propan-2-ol, (E) -5- (2-aminosulfonylamino-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vi-benzimidazole 2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl}. -phenyl) -propan-2-ol, 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl] -phenol, (2. {2- [2- (4- (4- (4-)} -butyl ester trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -carbamic acid, (2- {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl)] -1 H-benzimidazol-5-yl.} - phenyl) -methanol, (£) -N- { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl] - methanesulfonamide, (E) - (2. {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole-5- il.}.-phenyl) - ^ methanol, (E) -N- (2- { 1-methyl-2- [2- (4-triflu oromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} phenyl) -methanesulfonamide, (E) -N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -acetamide , (E) - (2- {2- [2- (4-Trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl} -carbamic acid tert-butyl ester, (£) -5- (2-methylsulfanyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, (E) -2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -5- (2-trifluoromethyl-phenyl-0-benzimidazole, (2) -2- {2 - [2- (2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5 -yl.}. -phenyl-2-ol, (E) -dimethyl- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. - benzyl) -amine, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} benzaldeh (E) -methyl- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzene amine, 2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl}. -benzylamine, (E) -5- (2-trmuoromethyl-phenyl) -2- [2- ( 4-trifluoromethyl-phenyl) -vinyl] -1H-15-benzimidazole, (E) -5- (2-trifluoromethoxy-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole , 2- [2- (2-phenylethynyl-1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-phenylethynyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, ( E) -5- (2-aminosulfonylamino-methylphenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, 2-. {2- 2- [2- (4-trifluoromethyl-phenylethynyl ) -1 H-benzimidazol-5-yl] -phenyl.}. -propan-2-ol, 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H- benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2- (2-. {2- 2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazole-5- il.}. phenyl) -propan-2-ol, 2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. -benzamide, N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole, 2- (2-. {2 - [(1 R, 2R ) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 2- (2- { 2 - [(1S, 2S) -2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1H-benzimidazol-5-yl. .phenyl) -propan-2-ol, 2-. { 2 - [(1S, 2S) -2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1H-benzamidezol-5-yl-benzenesulfonamide, 2- (2- ( 2-r (1S, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl-1 H-benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. {2 - [(1 R, 2S) -2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1 H -benzyldazol-5-yl.} - benzenesulfonamide, 2- (2 - {2 - [(1R, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol and 2- {2 - [(1S, 2R) -2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1H-benzyldazole-5-yl} - ^ benzenesulfonamide .
10. - The compound according to claim 9, further characterized in that the compound is selected from the group consisting of: (E) -1- (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanone, (E) -1- (2- {2- [2- (4-tert-butyl-fentl) -vinyl] -1H-benzimidazol-5-yl} - phenyl} (E) -2- {2- [2- (4-tert-Butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (£) -N- (2-. {2- 2- [2 - (4-tert-Butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -acetamide, (E) -2-. {2- [2- (4-ter- butyl-phenyl) -vinyl] -1H-benzimidazole-5-yl.] -benzamide, (E) -3- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -H -benzimidazol-5-yl}. -benzamide, (E) -4- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. .benzamide, (E) -N- (4- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide , (E) -N- (2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -methanesulfonamide, tert-butyl (E) - (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl} -carbamic acid ester (E) ) -2- { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.}.-Phenylamine, (E) - (2-. {2 - [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (E) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) ^ ethanone, (E ) -1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, (E) -N- ( 2- {2- (2- (4-trifluoromethy1-pheny1) -vin1] -1 H-benzimidazol-5-yl} - phenyl) -methanesulfonamide, (E) -2- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, (£) - 2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzamide, 5 (E) -1- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phen ethanone, (E) -1- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, (E) -N- (2 - { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) ^ methanesulfonamide, (E) -2- (2-. {2 - [2- (4-tnfluoromethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, (E) -N- (2-. {2- [2- (3,4-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -acetamide, or (E) -N- (3-. {2- 2- [2 - (3,4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, (E) -2-. {2- 2- (3,4- difluoro-phenyl) -vinyl] - H-benzimidazol-5-yl.} - benzamide, (E) -1- (2 { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H-benzimidazol-5-yl.}. -phenyl) -ethane (E) -N- (2- { 2- [2- (3,4-difluoro-phenyl) -vinyl] -1 H- benzimidazol-5-yl-phenyl) -methanesulfonamide, 2-. {2- [3- (4-tert-butyl-phenyl) -propyl] -1H-benzimidazol-5-yl} -phenol, 2- [3 - (4-tert-Butyl-phenyl) -propyl] -5-m-tolyl-1 H-benzimidazole , N- (2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} phenyl) -methanesulfonamide, 2-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 3-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, 4-. { 2- [2- (4-tert-Butyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenol, (E) - (2- { 2- [2- (4-trifluoromethylsulfanyl.-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (E) -N- (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, (E) -2 -. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} - benzamide, 0 (E) -1 - (2- { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, ( E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] - H -benzimidazol-5-yl.} - phenyl) -ethanone, (£ ^ -2- { 2- [2- (4-Trifluoromethanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (E) - (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) -N- ( 2- { 2- [2- (4-Trifluoromethanesulfonyl-pheny] -vinyl] -1 H -benzyldazol-5-yl.} - phenyl) -acetamide, (E) )-2-. { 2- [2- (4-Trifluoromethanesulfonyl-phenyl) -v] n-1] -1H-benzimidazol-5-yl} -benzamide, (E) -1- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl ) -ethanol, 1- (2- {2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl} -ethanol, (E) - 2- (2- { 2- [2- (4-Trifluoromethanesulfonyl-phenyl] -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol , (£) -2-. { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzyldazole-5-yl} -phenol, (£) -3-. { 2- [2- (4-tert-Butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzimidazol-5-yl} -phenol, (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl] -vinyl] -6-trifluoromethyl-1H-benzyldazole- 5-yl.}.-Phenyl) -acetamide, (E) - (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H- benzimidazol-5-yl.} - phenyl) -methanol, (E) -2- [2- (4-tert-butyl-phenyl) -vinyl] -5- (2-fluoro-phenyl) ) -6-trifluoromethyl-1 H-benzimidazole, (E) -2-. { 2- [2- (4-tert-butyl-pheny] -v] n-1] -6-trifluoromethyl-1 H-benzimidazol-5-yl} -benzamide, tert-butyl ester of (E) - (2- {2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1 H-benzimidazol-5-yl}-phenyl) -carbamic acid, (E) -N- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -6-trifluoromethyl-1H-benzimidazol-5-yl} -phenyl) -metanesulfonamide, (E) -N- (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzyl-5-yl}. phenyl) -acetamide, (E) -1- (2-. {6-trifluoromethyl-2- [2- (4-trifluoro-5-yl}. -phenyl) -ethanone, (E) - (2-. {6-trifluoromethyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -methanol, (E) - 2- {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -fe (/) -3-. {6-fluoro- 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimid (£) - (2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] - 1 H-benzimidazol-5-yl.} - phenyl) -methanol, (E) -1- (2. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H-benzimidazol-5-yl.} - phenyl) -ethanone, () -2-. {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole-5 -yl.}. -benzamide, (E) -N- (2-. { 6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} phenyl) -acetamide, (E) -N- (2- {6-fluoro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -methanesulfonamide, (E) - (2- {6-chloro-2- [2- (4-trifluoromethyl-phenyl) -v] n-1] -1H-benzamidazole-5- il.}.-phenyl) -methanol, (E) -1- (2. {6-chloro-2- [2- (4-trifluoromethyl-phenol) -vinyl] - 1 H-benzimidazol-5-yl.} - phenyl] -ethanone, (E) -2-. { 6-Chloro-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenol, (/ E) -2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-Trifluoromethanesulfonyl-phenyl) -v-n-1] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -N- (2- {2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) ) -2- (2- { 2- [2- (4-Chloro-phenyl) -v] nyl] -1 H -benzyldazole-5-yl.} - phenyl] - propan-2-ol, (E) -2-. { 2- [2- (4-chloro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (£) -2- (2- { 2- [2- (4-methanesulfonyl-phenyl) -v-n-1] -1 H -benzimidazol-5-yl}. ) -propan-2-ol, (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -N- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H- benzamdazol-5-yl) -phenyl] -methanesulfonamide, (E) -N- [2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propox !) -phenyl] -v! N! 1. -1 H-benzyldazol-5-yl) -phenyl] -metanesulfonamide, (E) -N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl] -1H-benzyldazol-5-yl] -phenyl) -methanesulfonamide, (E) -2- (2-. {2- 2- [ 2- (3-trifluoromethyl-phenyl] -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (4-tnfluoromethoxy-phenyl) -et N] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-chloro-phenyl) -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamida, 2-. { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl) -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Trifluoromethyl-phenyl) -cyclochlor] -1 H-benzimidazole-5-yl} -benzenesulfonamide, 2- (2- { 2- [2- (4-chloro-pheny] -cyclopropyl] -1 H -benzimidazole-5-yl.} -phenol) -propan -2-ol, 2- (2- { 2- [2- (3-tnfluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2- [2- (4-Trifluoromethyl-phenyl-1-yl) -1 H-benzimidazol-5-yl] -benzenesulfonamide > 2-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (3-trifluoromethyl-phenylethyl) -1 H -benzimidazol-5-yl] -benzenesulfonam (E-N-tert-butyl-2- { 2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, (£ ) - N -methyl-2- { 2- [2- (4-trifluoromethyl-phenyl) -v-n-1] -1H-benzyldazol-5-yl}. -benzenesulfonamide, (E) -2-hydroxy-1- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzyldazole-5-yl > -phenyl) -ethanone, (E) -2-. {2- 2- [2- (4-bromo-pheny] -vinyl] -1 H -benzimidazol-5-yl}. -N-methy1-benzenesulfonamide, (E) -N-methyl-2- [2- (2-p-tolyl-vinyl) -1 H-benzyldazole-5-yl] -benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-pheny] -v] n-1] -1 H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-dichloro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (3-bromo-4-fluoro-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-dimethylamine-phenyl) -v] nyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2-fluoro-4-trifluoromethy1-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, () -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (2, 3,4-trifluoro-phenyl] -v] nyl] -1 H -benzimidazole-5-yl} -benzenesulfonamide, (£) -N-methyl-2-. { 2- [2- (2/4 ^ 5-trifluoro-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,3-d.fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (2,5-difluoro-phenyl) -v-n-1] -1 H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2/6-difluoro-phenyl) -vinyl] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (£) -2 ^ 2- [2- (3/5-difluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (3 4-difluoro-phenyl) -vinyl] -1 H -benzyldazole-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-2-trifluoromethy1-phenyl) -v1n1] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenol) -v-n-1] -1H-benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (2-fluoro-3-trifluoromethyl-phenyl) -v] n-1] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (2/5-bis-trifluoromethyl-phenyl) -vin] -1-H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl] -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2-Chloro-6-fluoro-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (3-bromo-pheny] -vinyl] -1 H -benzimidazole-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1H-benzamidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -N-methyl-2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (4-Trifluoromethanesulfonyl-phenyl] -vinyl] -1H-benzimidazole-5-yl} -benzenesulfonamide, (E) -N-methyl-2-. { 2- [2- (2-trifluoromethyl-phenyl) -v-n-1] -1H-benzyldazole-5-yl} -benzenesulfonamide, (£) -N-methyl-2-. { 2- [2- (3-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -N-methyl-2-. { 2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (4-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2/4-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, N-methyl-2-. { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-difluoro-phenyl) -vinyl] -1H-benzyldazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (3,4-difluoro-phenyl) -v] nyl] -1 H -benzyldazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,3-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,5-d.fluoro-phenyl) -v.n.l) -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3,5-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-trifluoromethoxy-phenyl] -v] nyl] -1 H -benzyldazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-bromo-phenyl] -v] nyl] -1 H -benzyldazole-5-yl} -benzenesulfonamida, (_ )-2-. { 2- [2- (2-trifluoromethyl-phenyl) -v] n-1] -1H-benzyldazol-5-yl} -benzenesulfonamide, (iE -) - 2-. { 2- [2- (2-chloro-phenyl] -v] n-1] -1 H-benzimidazol-5-yl} -benzenesulfonamide > (£) -2-. { 2- [2- (2-bromo-phenyl) -v! Nl] -1 H-benzyldazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2y3J4-trifluoro-pheny1) -v1n1] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,4,5-trifluoro-pheny] -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2,6-difluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3,5-bis-trifluoromethyl-pheny] -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2/5-bis-trifluoromethyl-phenyl) -v] nyl] -1 H -benzimidazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-chloro-2-methanesulfonyl-phenyl) -vin] -1 H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-bromo-phenyl) -v] nyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-chloro-3-trifluoromethyl-phenyl) -v-n-1] -1H-benzyldazole-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (5-Bromo-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (4-trifluoromethylsulfanyl-phenyl] -v] nl] -1 H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-fluoro-3-trifluoromethyl-phenyl) -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,3,4-trifluoro-pheny] -etl] -1 H -benzimidazol-5-yl} -benzenesulfonamide > 2-. { 2- [2- (2,4,5-trifluoro-pheny] -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,6-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3,5-bis-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,5-bis-tnfluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Chloro-2-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Chloro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3-trifluoromethoxy-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,4-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3,4-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,3-difluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2,5-difluoro-phenyl) -ethyl] -1H ^ 2-. { 2- [2- (3,5-difluoro-phenyl) -ethyl] -H-benzimidazol-5-yl} -benzenesulfonamide, 2- (2-phenethyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, N, N-dimethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, N-methyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Fluoro-2-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (2-Fluoro-3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -N- (2- {2- [2- (4-bromo-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) ) -N- (2- { 2- [2- (4-isopropyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- ( 2- {2- [2- (3-chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) -N- (2 - { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- (2- {.2- [2- (4-difluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -methanesulfonamide, (.) -N- (2-. {2- [2- (3-fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (ÍE) -N-. { 2- [2- (2-p-tolyl-vinyl) -1H-benzimidazol-5-yl] -phenyl} -metansulfonamida, (£) -N- (2- { 2- [2- (4-dimethylamino-phenyl) -vinyl] -1H-benzimidazol-5-yl. L) -metanesulfonamide, (E) -N- (2- {2- [2- (4-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide , (£) -N-. { 2- [2- (2-naphthalen-2-yl-v, n-1) -1 H-benzimidazol-5-yl] -phenyl} -methanesulfonamide, (E) -N- (2- { 2- [2- (3J4-dichloro-phenyl] -v] nyl] -1 H -benzyldazol-5-yl.} - phenyl) - methanesulfonamide, (E) -N- (2- {2- [2- (3-fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide , (E) -N- (2- { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide , 2-. { 2- [2- (2-fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-Fluoro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, (E) -2-. { 2- [2- (3-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2-Fluoro-4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-ethoxy-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (£) -2- (2-styryl-1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -2-. { 2- [2- (3,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-chloro-2-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-isopropyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -2- [2- (2-p-tolyl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, (E) -2-. { 2- [2- (3-chloro-2-fluoro-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (3-Chloro-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2- [2- (2-naphthalen-2-yl-vinyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, (E) -2-. { 2- [2- (4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-difluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-Fluoro-5-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (£) -2-. { 2- [2- (2,4-dichloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (2-chloro-6-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (3-Bromo-4-fluoro-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -2-. { 2- [2- (4-ethoxy-phenyl) -vinyl] -1H-benzimidazole-5-N} -benzenesulfonamide, (£) -4-fluoro-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 2-. { 2- [2- (4-isopropyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -N- (2- {3-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -3H-benzimidazol-5-yl} -phenyl) -methanesulfonamide, (E) ) -4-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 4- tnfluoromethyl-2-. { 2- [2- (4-tnfluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -5-trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, 5- trifluoromethyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, (E) -1- [4- (2- {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl} -vinyl ) -phenyl-ethanone, (E) -2-. { 2- [2- (2-quinolin-6-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, (E) -N-isopropyl-4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl} -benzamide, (£) -2-. { 2- [2- (4-cyano-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -N- (4-. {2- 2- [2- (2-methylsulfamoyl-phenyl) -1 H -benzimidazo! -2-yl] -vinyl.}. -phenyl) -acetamide, Acid (E) -4-. { 2- [5- (2-methylsulfamoyl-phenyl) -1 H -benzimidazol-2-yl) -vinyl} -benzoic, (E) -2-. { 2- [2- (1 H-indol-6-yl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (E) -2-. { 2- [2- (2,4-bis-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, (£) -2-. { 2- [2- (4-acetyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -N-methyl-benzenesulfonamide, N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -acetamide, (E ) -2-2,2-trifluoro-N- (2- {2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -acetamide, 2- ({2- (2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (E) -2,2,2- Trifluoro-ethanesulfonic acid, (E) -2-dimethyl-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -propionamide, (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) -amide of (E) - ethanesulfonic acid (E) - (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl} -carbamic acid ester ( E) -2- (2- { 2- [2- (4-tert-butyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2 - (2- { 2- [2- (4-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, (E) -2- . { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} phenylamine, Ethyl ester of the acid (£) -2-. { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole-5-yl} -benzoic acid, N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} -phenyl] -methanesulfonamide , (£) -2- [2- (2-styryl-1 H-benzyldazol-5-yl) -phenyl] -propan-2-ol, (Z) -2- (2- { 2- [2- (4-trifluoromethyl-pheny] -vinyl] -1 H -benzyldazol-5-yl.} - phenyl) -propan-2-ol, (E) -5- (2-aminonosulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -v] nyl] -1H-benzimidazole, 2- (2-. {2- 2- [ 2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1H-benzyldazol-5-yl.} - phenyl] -propan-2-ol, 2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -nol, tert-butyl ester of (2- {2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} -phenyl} -carbamic acid, (2) - { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) -N-. { 2- [2- (2-biphenyl-4-yl-vinyl) -1 H -benzimidazol-5-yl] -phenyl} -methansulfonamide, (E) - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanol, (E) ) -N- (2- { 1-methyl-2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl-acetamide, tert-butyl ester of (E) acid - (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -carbamic acid, (E) -5- (2-methylsulfanyl) phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, (E) -2- [2- (4-trifluoromethanesulfonyl-phenyl) -v] nyl] -5- ( 2-trifluoromethyl-phenyl) -1H-benzimidazole, (E) -2- (2-. {2- [2- (2-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}-phenyl) -propan-2-ol, (E) -dimethyl- (2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzyl-benzyl) -amine, (£) -2- { 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-y (£) -methyl- (2-. {2- 2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.}. -benzyl amine, 2- { 2- [2- (4-tri. fluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -benzylamine, (E) -5- (2-trifluoromethyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazole, (E) -5- (2-trifluoromethoxy-phenyl) -2 - [2- (4-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazole, 2- [2- (2-phenylethenyl-1 H-benzimidazol-5-yl) -phenyl] -propan-2 -ol, 2- (2-phenylethynyl-1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -5- (2-aminosulfonyllamide-methylphenyl) -2- [2- ( 4-trifluoromethyl-phenyl) -vin benzimidazole, 2-. { 2- [2- (4-trifluoromethyl] phenylenyl] -1 H-benzimidazol-5-yl] -phenyl} -propan-2-ol ^ 2- (2- { 2- [2- (4-methoxy-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} -phenol) -propan- 2-ol, 2- (2- { 2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl.} -phenol) - propan-2-ol, 2-. { 2- [2- (4-trifluoromethyl-phenyl] -cyclopropyl] -1 H -benzyldazol-5-yl} -benzamida, N-tert-butyl-2-. { 2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, 5- (2-methanesulfonyl-phenyl) -2- [2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole, 2- (2-. {2 - [(1 R, 2R ) -2- (4-trifluoromethyl-pheny] -cyclopropyl] -1 H -benzyldazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2 - [(1 R, 2R) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl} - benzenesulfonamide, 2- (2-. {2 - [(1 S, 2S) -2- (4-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazole-5-yl. - phenyl) -propan-2-ol, 2-. { 2 - [(1 S, 2 S) -2- (4-trifluoromethyl-pheny] -cyclopropyl] -1 H -benzyldazole-5-yl} - benzenesulfonamide, 2- (2-l2-r (1 S, 2R) -2- (4-trifluoromethyl-phen-n-cyclopropyl-1 H-benzimidazol-5-yl-phenyl) -propan-2- ol, 2- {2 - [(1 R, 2S) -2- (4-trifluoromethyl-phenol) -cyclopropyl] -1H-benzim ^ benzenesulfonamide, 2- (2-. { 2 - [(1 R, 2S) -2- (4-Trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol and 2- {2 - [(1 S, 2R) -2- (4-trifluoromethyl-phenyl) -c-chloropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide.
1. The compound according to claim 9, further characterized in that the compound is selected from the group consists in: (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethoxy-phenyl) -vinyl] -1H-benzimidazol-5-yl} -phenyl) methanesulfonamide, (E) -C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl}. phenyl) -metanesulfonamide, (?) - 0,0,0 - ??????? -? - (2- { 2- [2- (4-1p ??? ^ ß? 3? 5 ?????? -? 6 ???) - ?????] - 1? - benzimidazol-5-yl.}.-Phenyl) -methanesulfonamide, (£) -1- (2- { 2- [2- (4-chloro-phenyl) -vinyl] -1H-benzimidazol-5-yl}. -phenyl) -ethanone, (E) -1- (2-. {2- 2- [2- (4-chloro-phenyl] -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanol, (E) -N- (2- { 2- [2- (4-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -phenyl) -C, C, C-trifluoro -metanesulfonamide, (E) -1- (2- {2- [2- (4-methanesulfonyl-phenyl) -v-n-1] -1 H-benzimidazol-5-ii.}. phenyl) -ethanone, (E) -1- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -ethanol , (£) -C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -vinyl] -1H-benzimidazol-5-yl} .-phenyl) -metanesulfonamide, (E) -1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] - vinyl.) -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (E) -1- [2- (2-. {2- 2- [4- (2,2,2- Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl. -1 H-benzimidazol-5-yl) -phenyl] -ethanol, (E) -N- [2 - (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl.} - 1 H -benzimidazol-5-yl) -phenyl ] -metanesulfonamide, (E) -2- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phen l] -v¡n¡l.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, (E) -2- (2- { 2- [4- ( 2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -fe nyl] -vinyl.} -1 H -benzimidazol-5-yl) -benzenesulfonamide, (E) -C, C, C-trifluoro-N- [2- (2-. { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- [2- (2-. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (E) -1- (2- (2-. {2- 2- 4- (2,2,2 -trifluoro-ethoxy) -phenyl] -v, n-1., -1 H-benzimidazol-5-yl) -phenyl] -ethanol, (E) -2- [2- (2- {.2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -v, n-1] -1 H-benzyldazol-5-yl) -phenyl] -propan-2-ol, (E) -2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -vinyl.} -1 H-benzimidazole-5 -yl) -benzenesulfonamide, (E) -CIClC-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] - vinyl.) -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- [2- (2-. {2- 2- [4- (2) 2,3, 3,3-pentafluoro-propoxy) -phenyl] -vinyl] -1 H-benzimidazol-5-yl) -phenyl] -ethanone, (E) -1- [2- (2 - { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -v / n. 1. -1 H-benzimidazol-5-yl. ) -phenyl] -ethanol, (E) -2- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -pheny] -v nil.}. -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, (E) -2- (2- { 2- [4- (2,2 , 3,3,3-pent afluoro-propoxy) -phenyl] -vinyl. -1 H-benzimidazol-5-yl) -benzenesulfonamide, (E) -C, C, C-trifluoro-N- [2- (2- { 2- [4- (21213 >3,3-pentafluoro-propoxy) -phenyl] -vinyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, (E) -1- (2- { 2- [2- (3-chloro-phenyl) -vinyl] -1 H- benzimidazol-5-yl.}. -phenyl) -ethanone, (E) -1- (2- { 2- [2- (3-chloro-phenyl) -v- ^^ (E) -N- ( 2- { 2- [2- (3-chloro-phenyl) -vin'yl] -1H-benzimidazol-5-yl.}.-Phenyl) -methanesulfonamide, (E) -2- (2-. { 2- [2- (3-chloro-phenyl] -vinyl] -1H-benzimidazol-5-yl.} - phenyl] -propan-2-ol> (E) -2 - { 2- [2- (3-Chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. -benzenesulfonamide, (E) -N- (2- { 2- [2 - (3-chloro-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -C, C, C-trifluoro-methanesulfonamide, (E) -1- (2-. {2 - [2- (3-trifluoromethyl-phenyl) -vinyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, (E) -1- (2-. {2- 2- ( 3-trifluoromethyl-phenyl) -vinyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanol, (£) -2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - benzenesulfonamide, (£) -C, C, C-trifluoro-N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -vinyl ] -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, (E) -N- (4-. {2- [5- (2-acetyl -phenyl) -1 H-benzimidazol-2-yl] -vinyl} phenyl) -metanesulfonamide, (E) -N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1H-benzimidazol-2-yl} -vinyl) phenyl] -metanesulfonamide, (£) -N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide , (E) -N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -vinyl) -phenyl] -methanesulfonamide, (£) -2-. { 2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -C, C, C-tnfluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -vinyl] -1 H -benzimidazol-5-yl}. phenyl) -metanesulfonamide, (£) -N- (4- { 2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -vinyl.} - phenyl) -C , C, C-trifluoro-methanesulfonamide, (E) -C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl.}. -vinyl) -phenyl] -methanesulfonamide, (E) -C, C, C-trifluoro-N- (4-. {2- 2- [5- (2-methanesulfonylamino-phenyl) -1 H-benzimidazol-2-yl] -vinyl.}. Phenyl) -methanesulfonamide, (E) -C, C, C-trifluoro-N- [4- (2-. {5- [2- ( 1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazol-2-yl.} - vinyl) -phenyl] -methanesulfonamide, (E) -2-. { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -vinyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, (E) -C, C, C-trifluoro-N- (4-. {2- 2- [2- (2-trifluoromethanesulfonylamino-phenyl) -1H-benzimidazol-2-yl] -vinyl.} - phenyl) -methanesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-tnfluoromethoxy-phenyl) -ethyl} -1 H -benzimidazol-5-yl} -phenyl ) -metanesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-trifluoromethyl-phenyl) -ethyl} -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, C, C, C-tnfluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 1- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -ethanone, 1-. { 2- [2- (4-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} phenyl) -ethanol, N- (2- {2- [2- (4-chloro-phenyl) -ethyl} -1 H -benzimidazol-5-yl} -phenyl) -methanesulfonamide, 2- ( 2- {2- [2- (4-chloro-phenyl) -ethyl} -1 H -benzimidazol-5-yl} -phenyl) -propan-2-ol, N- (2- { 2- [2- (4-chloro-phenyl) -ethyl] -1H-benzimidazol-5-yl]. -phenyl) -C, C, C-trifluoromethanesulfonamide, 1- (2-. {2 - [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.}. -phenyl) -et ^ c N- (2- { 2- [2- (4-methanesulfonyl-phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 2- (2-. {2- [2- (4-methanesulfonyl phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, C, C, C-trifluoro-N- (2-. {2- 2- ( 4-methanesulfonyl-phenyl) -ethyl) -1H-benzimidazol-5-yl} phenyl) -metanesulfonamide, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-tnfluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazole -5-yl) -phenyl] -ethanone, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.}. -1 H- benzimidazol-5-yl) -phenyl] -ethanol, 0 N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl) ] -ethyl.} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-tnfluoro-1-trifluoromethyl) -ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2-. {2- 2- [4- (2,2,2 -tnfluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2-. {2 - [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -ethyl.} - 1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- [2- (2 - { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanone, 5-1- [2- (2- {2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl} -1 H -benzimidazol-5-yl) -phenyl] -ethanol, N- [2 - (2- { 2- [4- (2,2,2-triflu gold-ethoxy) -phenyl] -ethyl} -1H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -ethyl.}. -1H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenol ] -ethyl.} -1 H-benzyldazol-5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2- { 2- [4- (2, 2,2-trifluoro-ethoxy) -phenyl] -ethyl.} -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 0 1 - [2- (2- { 2- [4- ( 2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2-. {2 - [4- (2, 2,3,3, 3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2 - { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -ethyl.} -1 H-benzimidazole-5 -yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-pr opoxy) -phenyl] -ethyl} -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- (2- { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} .-phenyl) -ethanone, 1- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethane N- ( 2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- 2- [2. - (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, 2-. { 2- [2- (3-Chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, N- (2- { 2- [2- (3-chloro-phenyl) -ethyl] -1 H -benzimidazol-5-yl.}. -phenyl) -C, C, C-tnfluoro- methanesulfonamide, 1- (2- {2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1H-benzimidazol-5-yl} -phenyl) -ethanone, 1 - . 1 - (2- { 2- [2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-ylH ^ N- (2- { 2- [2- (3-trifluoromethyl) -phenyl) -ethyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- 2- (3-trifluoromethyl-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -propan-2-ol, C > C, C-trifluoro-N- (2- {2 - [2- (3-trifluoromethyl-phenyl) -ethyl} ) -1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] - ethyl.}. phenyl) -metanesulfonamide, N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -ethyl ) -phenyl] -metanesulfonamide, N- (2- { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, N- [4- (2- { 5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - ethyl) -phenyl] -methanesulfonamide, 2 -. { 2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -phenyl) - methanesulfonamide, N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl] -ethyl] -phenyl) -C, C, C-trm-methanesulfonamide, C, C, C-trifluoro-N- [4- (2- {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl} -ethyl) - phenyl] -methanesulfonamide, C, ClC-trifluoro-N- (4-. {2- 2- [2- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] -ethyl} - phenyl) - methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazole-2-yl}. .ethyl) -phenyl] -methanesulfonamide, 2-. { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -ethyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 2-. { 2- [2- (4-trifluoromethoxy-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, 2-. { 2- [2- (4-trifluoromethanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2. {2- [2- (4-trifluoromethoxy-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} .-phenyl) -methanesulfonamide, C >; C, C-trifluoro-N- (2-. {2- 2- [2- (4-trifluoromethy1-pheny1) -cyclopropyl] -1 H- ^ benzimidazol-5-yl} .-pheny!) -metanesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonyl-phenol) -cyclopropyl] -1 H- benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 1- (2- { 2- [2- (4-chloro-pheny] -cyclopropyl] -1 H-benzim Dazol-5-yl.} - phenyl] -ethanone, 1- (2- { 2- [2- (4-Chloro-pheny] -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanol, N- (2 - { 2- [2- (4-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2-. { 2- [2- (4-chloro-pheny] -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, N- (2-. {2- 2- [2- (4-chloro-phenyl] -cyclopropyl] -1 H -benzimidazole-5-yl.} - phenyl) -C , C, C-j Q trifluoro-methanesulfonamide, 1- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) - ethanone, 1- (2- { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzyldazol-5-yl}. -phenyl] - ethanol, N- (2-. {2- 2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzyldazol-5-yl.} - phenyl) - methanesulfonamide, 2- (2- { 2- [2- (4-methanesulfonyl-pheny] -cyclopropyl] -1H-benzimidazole-5-yl.} -phenol) -propan-2-ol , 2-. { 2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1 H -benzyldazole-5-yl} -15-benzenesulfonamide, C, C, C-trifluoro-N- (2- {2- [2- (4-methanesulfonyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - phenyl) -metanesulfonamide, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} - 1 H- benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phen L] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- 4- (2,2,2- trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-Trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl] -1 H-20-benzimidazol-5-yl) -phen L] -propan-2-ol, 2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenyl] -cyclopropyl} -1H-benzimidazole -5-yl) -benzenesulfonamide, C, C, C-trifluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) - phenol] -cyclopropyl-1-H-benzimidazole-Si-phenyl-methanesulfonamide, 1- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] - DC lo-propyl) -1 H-benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2-. { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl] -cyclopropyl. -1 H-benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy) -phenyl) -cyclopropyl} -1H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2- (2- { 2- [4- (2,2,2-tnfluoro-ethoxy) -phenyl] -cyclopropyl.} -1 H-benzimidazol-5-yl) -, - benzenesulfonamide, C, C, C-tnfluoro-N- [2- (2- { 2- [4- (2,2,2-trifluoro-ethoxy ) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 1- [2- (2-. {2- 2- [2,2,3,3, 3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -ethanone, 1- [2- (2-. {2- 2- (4- (2,2 , 3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -ethanol, N- [2- (2-. {2- 2- [4 - (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H -benzimidazol-5-yl) -phenyl] -methanesulfonamide, 2- [2- (2-. { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl] -1 H-benzimidazol-5-yl) -phenyl] -propan-2-ol, 2 - (2- {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl} -1 H-benzimidazol-5-yl) -benzenesulfonamide, C, C, C-tnfluoro-N- [2- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenyl] -cyclopropyl.] -1 H-benzimidazole -5-yl) -phenyl] -metans ulfonamide, 1- (2-. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} phenyl) -ethanone, 1- (2- {2- [2- (3-chloro-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -phenyl) -ethanol, N- (2-. {2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- [2- (3-chloro-phenyl) ) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -propan-2-5 0 | -2. { 2- [2- (3-Chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - benzenesulfonamide, N- (2- { 2- [2- (3-chloro-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -C, C, C-trifluoro- methanesulfonamide, 1- (2-. {2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -ethanone, 1- (2-. { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl}. -phenyl) -ethanol, N- (2-. {2- 2- (3- (3- trifluoromethyl-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -0-methanesulfonamide, 2-. { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (3-trifluoromethyl-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide , N- (4- { 2- [5- (2-Acetyl-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl.} - phenyl) -methanesulfonamide, N- [4- (2- { 5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl}. -cyclopropyl) -phenyl] -methanesulfonamide, N- (2- {2- [2- (4-methanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl} - phenyl) -methanesulfonamide, N- [4- (2- { 5- [2- (1-Hydroxy-1-methyl-ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl phenyl] -methanesulfonamide, 2-. {2- 2- [2- (4 -metanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - benzenesulfonamide, C, C, C-trifluoro-N- (2-. {2- 2- [2- (4-methanesulfonylamino-phenyl ) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) -methanesulfonamide, N- (4-. {2- [5- (2-acetyl-phenyl) -1 H -benzimidazole-2- il] -cyclopropyl.}.-phenyl) -C, C, C-trifluoro-methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2- (1-hydroxy) ethyl) -phenyl] -1 H -benzimidazol-2-yl.} - cyclopropyl) -phenyl] -methanesulfonamide, C, C, C-trifluoro-N- (4-. {2- [5- (2- methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl] -cyclopropyl.} - phenyl) -methanesulfonamide, C, C, C-trifluoro-N- [4- (2-. {5- [2- ( 1-hydroxy-1-methyl-ethyl) -phenyl] -1 H-benc imidazol-2-yl} -cyclopropyl) -phenyl] -methanesulfonamide, 2-. { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1H-benzimidazol-5-yl} -benzenesulfonamide, C, C, C-trifluoro-N- (2- { 2- [2- (4-trifluoromethanesulfonylamino-phenyl) -cyclopropyl] -1 H -benzimidazol-5-yl.} - phenyl) - methanesulfonamide, 2- [2- (4-trifluoromethoxy-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, 2- [2- (4-trifluoromethanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] - benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-tN-fluoro-methoxy-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl-methanesulfonamide, phenyl-methanesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 1-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 1-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanol, N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 2- . { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, N-. { 2- [2- (4-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -C, C, C-trifluoro-methanesulfonamide, 1-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanone, 1- . { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl-phenyl} -etanol, N-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -metanesulfonamide, 2-. { 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, 2- [2- (4-methanesulfonyl-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonyl-phenylethyl) -1 H-benzyldazol-5-yl] -phenol} -methansulfonamide, 1- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazole-5-yl.} - phenyl) -ethanone, l ^^ - H ^^^ - trifluoro-l-trifluoromethyl-ethoxy-phenylethyl-1H-benzimidazol-5-yl} phenyl) -ethanol, N- (2 ^ 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy-phenylethynyl] -1 H -benzimidazole- ^ 5-yl.} - phenyl) -methansulfonamide, 2- (2- { 2- [4- (2,2,2-trifluoro-1-trifluoromethyl-ethoxy) -phenylethynyl] -1 H -benzimidazole-5-yl. .-phenyl) -propan-2-ol, 2- { 2- [4- (2,2,2-tnfluoro-1-trifluoromethyl-ethoxy) -phenylethyl] -1 H-benzimidazole- 5-yl] -benzenesulfonamide, C, C, C-trifluoro-N- (2. {2- 2- [4- (2,2,2-tnfluoro-1-tnfluoromethyl-ethoxy) -phenylethynyl] - 1 H-benzimidazole-5-yl.] - phenyl] -metanesulfonamide, 1- (2. {2- 2- [4- (2,2,2-trifluoro-ethoxy) -phen Letinyl] -1 H-benzyldazol-5-yl.} - phenyl] -ethanone, 1- (2-. {2- 2- [4- (2,2,2-trifluoro) -ethoxy) -phenylethynyl] -1H-benzimidazol-5-yl.}. -phenyl) -0 ethanol, N- (2-. {2- 2- [4- (2,2,2-trifluoro- ethoxy) -phenylethyl] -1 H-benzimidazol-5-yl.] -phenyl) -methanesulfonamide, 2- (2-. {2- 2- [4- (2,2,2- trifluoro-ethoxy) -phenylaletinyl] -1H-benzamidazol-5-yl.] -phenyl] -propan-2-ol, 2- { 2- [4 - (2,2,2-trifluoro-ethoxy) -phenylethyl] -1 H-benzimid azol-5-yl.} - benzenesulfonamide, C, C > C-trifluoro-N- (2. {2- (4- (2> 2,2-trifluoro-ethoxy) -phenylethyl) -1 H -benzyldazole-5-yl. L) -metanesulfonamide, 1- (2- { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenollet] -1 H-benzimidazole- 5-yl.) -5-phenyl) -ethanone, 1- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethyl] -1 H -benzimidazole-5-yl.} - phenyl) -ethanol, N- (2. {2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenylethyl] - 1 H-benzimidazol-5-yl.} - phenyl) -methanesulfonamide, 2- (2-. {2- 2- [4- (2,2,3,3,3-pentafluoro-propoxy) phenylethyl] -1H-benzimidazol-5-yl.} - phenol) -propan-2-ol, 2-. { 2- [4- (2,2,3,3,3-pentafluoro-propoxy) -phenollet] -1 H-benzimidazol-5-yl} - benzenesulfonamide, C, C, C-trifluoro-N- (2-. {2- 2- [4- (2, 2,3,3, 3-pentafluoro-propoxy!) -phenylethynyl] -1H-0-benzamidazole -5-yl.}.-Phenyl) -methanesulfonamide, 1-. { 2- [2- (3-chloro-phenylene] -1 H-benzimidazol-5-yl] -phenyl} -etanona, 2-. { 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -propan-2-ol, N-. { 2- [2- (3-Chloro-phenylethynyl) -1H-benzimidazol-5-yl] -phenyl} -metanesulfonamide, 1- . { 2- [2- (3-Chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} Ethanol, 2- [2- (3-chloro-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, N-. { 2- [2- (3-Chloro-phenylethyl) -1 H-benzyldazol-5-yl] -phenyl} -C, C, C-trifluoromethanesulfonamide, 1-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzimidazol-5-yl] -phenyl} -etanona, 1-. { 2- [2- (3-trifluoromethyl-phenletin) -1 H-benzimidazol-5-yl] -phenyl} -etan N-. { 2- [2- (3-trifluoromethyl-phenylethynyl) -1 H -benzyldazol-5-yl] -phenyl} - methanesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (3-Trifluoromethy1-phenyletyl] -1 H-benzimidazol-5-yl] -phenyl} -metansulfonamida, N-. { 4- [5- (2-acetyl-phenyl) -1 H -benzimidazol-2-yl-ethyl] -phenyl} -metanesulfonamide, N- (4-. {5- [2- (1-Hydroxy-ethyl) -phenyl] -1 H -benzyldazol-2-yl-ethynyl} -phenyl ) - methanesulfonamide, N-. { 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzyldazol-5-yl] -phenyl} methanesulfonamide, N- (4-. {5- [2- (1-hydroxyl-1-methyl-ethyl) -phenyl] -1H-benzyldazole-2-yl-ethynyl} phenyl) -methanesulfonamide, 2- [2- (4-methanesulfonylamino-phenylethynyl) -1 H -benzimidazol-5-yl] -benzenesulfonamide, C, C, C-trifluoro-N-. { 2- [2- (4-methanesulfonyllamine-phenylethenyl) -1 H-benzimidazol-5-yl] -phenyl} -metansulfonamide, N-. { 4- [5- (2-acetyl-phenyl) -1 H-benzimidazole-2-M methanesulfonamide, C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-ethyl) -phenyl] -1 H -benzimidazol-2-yl-ethynyl-phenyl ) -metanesulfonamide, CIC, C-trifluoro-N-. { 4- [5- (2-methanesulfonylamino-phenyl) -1 H -benzimidazol-2-yl-ethyl] -phenyl} -methansulfonamide, C, C, C-trifluoro-N- (4-. {5- [2- (1-hydroxy-1-methyl-ethyl) -phenyl] -1H-benzimidazo ^ ethynyl.}.-pheny] -metanesulfonamide, 2- [2- (4-trifluoromethanesulfonylamino-phenylethenyl) -1 H -benzyldazol-5-yl] -benzenesulfonamide and C, C, C -trifluoro-N-. { 2- [2- (4-trifluoromethanesulfonyl-phenylethyl] -1 H-benzimidazol-5-yl] -phenyl} -metansulfonamide.
12. - A salt of the compound of claim 1 selected of the group consisting of acetate, adipate, benzenesulfonate, benzoate, bicarbonate, bisulfate, bitartrate, borate, bromide, calcium, camsylate (or camphor sulfonate), carbonate, chloride, choline, clavulanate, citrate, dihydrochloride, disodium, edetate, fumarate, gluconate, glutamate, hydrabamine, hydrobromide, hydrochloride, iodide, isothionate, lactate, malate, maleate, mandelate, mesylate, nitrate, oleate, pamoate, palmitate, phosphate / diphosphate, salicylate, sodium, stearate, sulfate, succinate, tartrate, trometan, tosylate, trichloroacetate and trifluoroacetate.
13. - The salt according to claim 12, further characterized in that the salt is selected from the group consisting of disodium, hydrochloride and sodium.
14. - A pharmaceutical composition comprising the compound of claim 1 and one or more vehicles, excipients or diluents acceptable for pharmaceutical use.
15. - A use of the compound of claim 1 for the manufacture of a medicament useful for treating a disease mediated by the ion channel VR1, where the disease mediated by the ion channel VR1 is chronic or acute pain due to a disease causing pain inflammatory, burning pain or postoperative pain.
16. - The use as claimed in claim 15, wherein the effective amount of the compound of claim 1 is in the range of about 0.001 mg / kg / day to about 300 mg / kg / day.
17. - A process for the preparation of the compound of claim 1 comprising the steps of: Step A: reacting an aldehyde QQ1 with masonic acid and a catalytic amount of piperidine in pyridine at elevated temperatures to provide a QQ2 acid: Step B: react the QQ2 acid with oxalyl chloride and a catalytic amount of DMF in a solvent such as methylene chloride to provide a QQ3 acid chloride: Step C: react the QQ3 acid chloride with 4-bromobenzene-1,2-diamine AA1 in acetic acid to provide a bromobenzimidazole QQ4: ; and Step D: reacting the bromobenzimidazole UU with an appropriately substituted phenyl boronic acid in the presence of a reagent and a catalytic amount of a palladium catalyst in a solvent to give a benzimidazole substituted with alcohol QQ5, representative of a compound of Formula (I) ):
MX2008014108A 2006-05-03 2007-04-17 Benzimidazole modulators of vr1. MX2008014108A (en)

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